


Discovering Dean (Sweet Creature)

by Wings_of_Cas



Category: Supernatural
Genre: Bottom Dean Winchester, I will add tags as I go on with the story, M/M, Maybe we're not sure yet, Mechanic Dean Winchester, Multi, Panties Kink, Police Officer Castiel (Supernatural), Rape/Non-con Elements, Sex Worker Dean Winchester, Team Dean Winchester's Red Ass, Top Castiel (Supernatural)
Language: English
Status: In-Progress
Published: 2020-04-09
Updated: 2020-05-08
Packaged: 2021-03-01 19:42:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 20,527
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23552497
Author URL: https://archiveofourown.org/users/Wings_of_Cas/pseuds/Wings_of_Cas
Summary: Sam's been off to Stanford for about a year and Dean's been juggling two jobs just to support him. He works for Bobby, of course, but he's lied to everyone else about his second job. What would they all think if they knew Dean got on stage almost every night in frilly panties and gave private dances to seedy customers in even seedier backrooms? Even if he wanted out, he couldn't afford it and he doubts Crowley would ever let him break his contract with "The Rack".Castiel Novak is a marine veteran and as is traditional for his family, joined the police force soon after his enlistment ended. He's not particularly happy with his work (or his family), but gains a renewed interest in his job when his brother puts him on a case concerning a night club called "The Rack". It's run by a particularly tricky businessman named Crowley and it's Castiel's job to find a way to shut it down.When Dean and Castiel meet, they have no way of knowing how important they will become to each other. However, what will Dean do when he realizes that Castiel is trying to take away his one shot at putting Sam through Stanford? And what will Castiel do when he realizes Dean is not just an ordinary mechanic?
Relationships: Castiel/Dean Winchester, Dean Winchester/Other(s), Jessica Moore/Sam Winchester, Michael/Dean Winchester, Ruby/Sam Winchester
Comments: 53
Kudos: 77





	1. Dean

**Author's Note:**

> Hey guys! First of all, thank you for even clicking on this story at all! This is the first time I've written fanfiction in many years and honestly, I'm super nervous. I will update the tags and warnings as I continue with the story, but know that I will always place appropriate warnings at the beginning of each chapter if need be. I love hearing from people so please feel free to leave me a comment! I hope you enjoy!

**Notes for the Chapter:**

> **This chapter has been edited and improved

Dean does _not_ whine when his body finally hits his bed. He does, however, when his phone starts ringing. There are only two people in the world that would dare call him at two thirty in the goddamn morning and one of them is presently snoozing in the room across from his. That leaves only one culprit; a certain floppy haired, rabbit food munching dork currently residing in California. The same floppy haired dork who continuously forgets to take _time zones_ into account.

“Sammy?” Dean knows he sounds wrecked, but he had to work a double shift for Bobby and then another at the club straight afterwards. Saturday nights are always busy at the club and he’d been booked back to back and then… Alistair had been there. Dean’s fingers soothe over the ache in his throat at Alistair’s memory, but then he catches himself and shakes his head because _fuck that noise, that’s why_. He clears his throat and aims for less gravel this time. “You good, Sammy?”

“ _Dean_.” Sam’s voice is urgent and tinny sounding through the phone and yeah, it looks like Dean’s not going to get his four hours of sleep after all, because his little brother needs him right now and Sammy always comes first. “Dean. Is this a bad time?”

“There’s never a bad time for you, Sam. You know that.” When Sam says nothing back, he rubs his face in exhaustion and makes himself sit up. He grunts when his shirt brushes against his still tender back but swallows his pain down the best he can. “What’s wrong, Sammy?”

“Nothing’s wrong. Well, I mean, there’s something, but it’s not bad and I totally understand if you don’t wanna do this right now because – ”

“ _Today_ , Sam.”

“There’s a girl!”

Dean pauses at what his little brother has just blurted out. He breathes in, shaky, and lets it back out as he nods to himself because _girls_. Girls are something Dean can work with. Really, out of all the reasons Sam would call him so early in the goddamn morning, he hadn’t been expecting _this_ , but Sammy’s okay and this is something he can handle. And now that he knows that Sam’s not in any kind of danger, he’s calmed down enough that he can even hear music and people in the background on Sam’s end.

“Are you – are you at a _party_?”

He doesn’t need to see Sam to know that he’s rolling his eyes.

“I’m at college, Dean. What did you expect?”

“Honestly? For you to be nerding it up in the library every night, Urkel. Not that I’m complaining. It’s just nice that you’re… that you’ve... you know – ”

“ _Dean_.”

That sounds like Sam’s pulling bitch face #7. He coughs. “Right, the girl. Catch me up. What’s going on?”

“Her names Ruby.” Sam swoons and Dean can’t help the way he grins. He’ll make sure to tease his little brother about this later. “She wicked smart and gorgeous and she has this, like, superpower where she makes it feel like the world’s slowing down and – ”

“Okay, okay. And what? You want to kiss this girl?”

“I want to take her out on a date, Dean!”

It’s Dean’s turn to roll his eyes at Sam’s scandalized tone.

“Alright, Samantha, calm down. Have you asked her out on one yet?”

“…No.”

Dean rubs his eyes and looks at the clock on his bedside. 2:42am. “Alright,” he sighs, fighting down the exhaustion seeping into his bones. “Alright, well that’s probably the best place to start, kiddo.”

“I’m not you, Dean. I can’t just walk up to the coolest girl at the party and ask her out on a date.”

“Sure you can, Sammy. What girl in her right mind is going to turn down those big puppy dog eyes?”

“ _Dean_.”

“Okay, okay. Just let me think.” It’s quiet for a moment while they both collect their thoughts. Dean’s cursing the sound of the hollers and cringey dance music radiating from Sam’s end when a thought finally strikes him. “Hey, Sammy… who invited you to this party anyway?”

The long pause before Sam answers is telling. “Ruby…”

Dean’s going to noogie the crap out of that kid the next time he sees him. “Damn it, Sam! Okay listen; this is what you’re going to do. Just walk up to the girl – Ruby, I get it, _Ruby_ – and tell her that you want to thank her for inviting you to the party. When she does her whole ‘ _oh, it’s no problem_ ’ thing, tell her that you’d really like to thank her properly and invite her out to lunch sometime. Make sure you use your big, dumb googly eyes. Girls eat that crap up like it’s candy.”

It’s a testament to how well Dean knows Sam, that he can tell from his gentle breathing on the other end that the poor kid is overthinking every single possible scenario and outcome. He must like the plan, though, because after a moment Sam comes out of his head to hesitantly ask “do you really think that will work, Dean?”

“Dude. You’re adorable! You’re good looking and smarter than any of those other guys at Stanford. And you like salads! Chicks like salads! Anything would work for you, Sammy, but _this_? This will work. I promise.”

“We seriously need to have a talk about your eating habits, Dean, but, um… thank you. Really. I’m lucky to have a big brother like you.”

Dean rolls his eyes but that doesn’t stop his entire chest from warming up at just how freakin’ appreciative Sam sounds. It’s been a year since Sam left him behind for bigger and better things and damn it, Dean _misses him_. When Sam had first left for college, he was getting calls twice a day every day just so he could hear him rave on about ‘ _Stanford this_ ’ and ‘ _Stanford that_ ’, but as the months have passed, Dean’s lucky to get a call every other week.

He gets it though. There’s no life for Sam is Sioux Falls and when he was home, Dean was just holding him back. If the roles were reversed, Dean probably would have left him too. Sammy has always deserved much more than what he and Dad could ever offer him anyway.

He purses his lips and rubs his hands on his jeans. He’s too mentally and physically tired to go down that rabbit hole again. If he’s lucky, he’s tired enough that he won’t have to be left alone with his thoughts and he can just drift off.

“Yeah, yeah, Samantha. Don’t go crying on me, now. I gotta get some sleep anyway.”

“Yeah, right. _Right_.” Sam clears his throat and then quietly adds: “I miss you, Dean.”

“Yeah. I miss you too, Sammy.” He whispers back, just as gently, careful not to ruin their moment. They don’t get many like these anymore. “Don’t be a stranger, ya hear?”

“I promise.”

“Night, bitch.”

“Jerk.” And then Sammy’s gone. Dean stares at his phone, eyes hot and stinging, before tossing it to the side with a growl. He rips off his shirt and regrets it instantly when the fabric tugs at the raised flesh on his back from where Alistair had paddled him earlier. Stifling his wince, he throws his shirt onto the ground and strips the rest of the way down into only his boxers. He’s only just managed to get under his covers when a yawn startles his attention to his own doorway.

Benny’s there, scratching his scruff and looking for all the world like a bear that’s just come out of hibernation.

“Everythin’ alright, brother?” Benny’s voice is gruff and sleep heavy and instantly, Dean melts into the feeling of _safety_ and _home_.

“Yeah, Benny. Everythin’s alright. Get back to bed.”

His best friend regards him with one last concerned look over before nodding to himself, still looking doubtful. “Alrigh’. You just holler if ya need me, brother, ya hear?”

Dean agrees just to put him at ease and with that, Benny lumbers back to his own bedroom, pawing at his stomach as he goes. When Dean chances another look at his clock, it’s already 2:58am and he has to be awake in three and a half hours. He groans mournfully and rubs his face into his pillow.

Between the aches in his body and the way his mind races, it’s a struggle for Dean to fall asleep but when he finally does, it’s like slipping into deep, dark seas. It’s the feeling of floating and suffocating and not knowing what’s waiting for him in the darkness all at once. But deep down Dean knows whose waiting for him there.

He dreams of those faces every night.

†

“You look like hell, boy.” Bobby grumbles in way of greeting.

Dean snorts and takes the beer the old man offers him anyway. “Gee, thanks, Bobby. You always sweet talk the ladies like this or am I just special?”

“Idjit.” Bobby mutters, shaking his head with a chuckle. Dean just rolls his eyes fondly and takes a sip of his beer, shoulders relaxing as he does so. He’s still beat from the day before and the constant onslaught of work today hasn’t helped any. He feels like a stiff wind could just topple him over and honestly, he might just let it happen if it means he gets to take a quick nap. The old man must notice how tired he is because he leans back and leers at him long enough to make him uncomfortable.

Dean fiddles with a cloth almost as dirty as his oil-stained hands and tries not to look too guilty. “You gonna ask me to the prom, Bobby?”

“You’re working yourself into the ground, boy.”

“Not this again. Give it a rest, man – ”

“I _mean it_ , Dean. You look like you haven’t slept in years. When was the last time you took a day off?”

 _Years_ , Dean’s traitor mind supplies unhelpfully. Ignoring that thought, he toes at the ground with his boot and takes another swig of his beer. His silence is telling and Bobby shakes his head.

“Exactly.” He spits and this time, there’s heat to it.

“What do you want me to do, Bobby?” Dean huffs, throwing himself back under the hood of the car he’s working on. Anything to avoid that pained look Bobby gets on his face sometimes when the old man thinks too hard about him. “Someone has to pay for Sam to go to college and I don’t know if you know this, but Dad hasn’t been around for a while.”

“It’s not your responsibility, Dean. Your Daddy should have – ”

“Should have _what_ , Bobby?” Dean hisses, whipping around to face the old man and regretting it instantly when he sees that _damned_ look on his face; like someone’s just torn his heart right out of his chest. It only serves to make him feel more defensive. “Dad should have _what,_ Bobby? _Stayed_? Because that was going so well between he and Sam fighting all the damn time, and all those drunken nights! Or do you mean something else? Should he have not dragged us around the country for all of our childhoods? Should he have _raised us_ or you know what – pretended like he at least _cared_? Newsflash, Bobby: even when Dad was around, he wasn’t there! I’m the one who cooked Sam dinner. _I’m_ the one who tucked him into bed at night and when he needed a new pair of shoes for school, _I’m_ the one who got a job to pay for them! I’ve been raising that boy since the day Mom died and you know what – I’m going to keep doing that until he realizes he don’t need me no more. I’m dead weight and right now, Stanford is Sam’s only chance at being something _better_ than me and Dad. So yeah Bobby, I’m tired. I’m _spent_. But I – I just have to – Sam needs – ”

His voice cracks and he falters, the ugly words he’s been hiding deep down inside himself for quite some time now caught in his throat. He shouldn’t talk about Dad like that. The man’s led a hard life and honestly, he’s not surprised he left to go live with his new family. Dean’s not easy to be around and… he coughs and roughly palms at his eyes, disgusted with himself when his hands come back a little wet.

And shit. He’s just yelled at Bobby in the middle of his own damn business just because the old man was worried about him. He yelled at _Bobby_. He really must be more run down than usual.

He sniffs and squares his shoulders, straightening up to look the old man in the eye and apologize to him like a man when the guy just shakes his head, his eyes a little red too. He hates that he’s the one that put that look on such a good man’s face.

“Come here you stupid son of a bitch.” Bobby mutters and Dean’s suddenly pulled into a tight hug, his face pressed into Bobby’s old, weathered vest as those arms wrap tightly around him. Those arms are pressed smug against his still sore back and despite Dean having to bite back a wince, he allows himself to sag into the touch for just a moment. “You’re not dead weight, you hear me? You’ve done right by your brother and you’re a damned good kid. You’re smart and you’re hard working and you deserve so much better than what the world has handed you, son. You’re just so damned busy looking after everyone else, you haven’t done the same for you yet.”

“Alright, Bobby.” Dean says, sounding small and not quite ready to move away. But he does anyway, patting the old man’s back as he goes. “Are we done or do you want to braid each other’s hair now?”

Bobby takes him by the shoulders and gives him a stern look. “Dream on, boy.”

Dean shakes his head and then Bobby’s patting his arm and stepping back. He has a feeling this conversation isn’t over – it never really is – but he’s surprised when Bobby doesn’t drop it right away.

“I’m giving you tomorrow off.”

“ _What?_ Bobby – ”

“Don’t even try sayin’ you can’t afford it, neither.” Bobby growls and Dean slams his mouth shut at the serious warning in that voice. “You’ve been covering everybody else’s shifts this whole damn month and you’re still working that other job – the bartending, or whatever you say it is. You can take a _day_ for yourself, Dean.”

Dean wants to argue. He really does, but the truth is, he doesn’t remember the last time he actually got a full night’s sleep, and he doesn’t even work at the club on Mondays since he’s the main event Friday through Sunday. It would be a real, full, honest to God actual day off work and come to think of it, he could really use one of those. Baby’s been itching for a tune up and he could even call Sam and ask him how things went with that Ruby chick. 

“Alright, Bobby.” He says gruffly. “I’ll take the damn day off. Anything else you need, princess?”

“Yeah.” Bobby mutters, sounding pleasantly surprised. “Get back to work and stop wasting company time, ya idjit.”

Dean laughs hard at that and does as he’s told, practically buzzing over the prospect of having something to look forward to tomorrow _. A whole damn day off_ , he thinks, shaking his head incredulously. And damn, if that’s all it takes to make Bobby happy, he’ll volunteer as tribute any damn time.

 _Though_ , he pauses, a deep frown settling on his face. _I really should make it up to the old man for treating him the way I did._

A man like Bobby don’t deserve the kind of crap he just got. Not when the man salvaged he and Sam’s childhoods the best he could. Shit, that man was the first person to try and play ball with them.

With shame burning in his gut, he sets out to work even harder than before.


	2. Dean

**Notes for the Chapter:**

> Hey guys! Sorry this chapter is coming out a day later than promised! I went back and forth with it a lot as I was working on it. There is a little Michael in this chapter and a bit more background too! Also, Cas will be introduced in the next chapter, so don't worry - I haven't forgotten about our sweet, loyal angel. He's just waiting for his big moment.
> 
> I hope you guys enjoy! As always, feel free to leave me comments and feedback! Thank you for reading!
> 
> **This chapter has been edited and made better

Dean’s balancing two burgers, a large fry and a couple of beers in his arms when he kicks the door to Bobby’s office open. The old man takes a second to raise a brow at him before he starts clearing his desk. “What’s all this?”

“Count it as an apology.”

“Well, apology accepted.”

Dean spills their lunch onto the desk with a relieved sigh, before falling into the nearest chair across from Bobby. He takes a burger, unwraps it and takes a bite so big that one his cheeks puff out like he’s a cartoon character. When he was young and used to eat burgers with his Dad on the road, Dean would always imagine he was Shaggy from Scooby-Doo and take as big a bite as his tiny little mouth would allow. The habit’s stuck with him ever since. Chuckling at the memory, Dean glances back up and pauses when he sees Bobby’s look of abject horror.

“Wha’f?”

“The burger ain’t gonna run away, son.”

Dean swallows his bite – with some difficulty – and grins. When all Bobby does is shake his head fondly at him and start on his own burger, Dean squirms in his chair and sets his food down so he can pick up his beer. He suddenly doesn’t have the stomach for that either, so he starts to peel at the label instead. “You know, Bobby… about what happened earlier…”

Bobby gives him a pointed look that has his ears burning. “You don’t need to apologize, Dean. Like I said; you’ve been over workin’ yourself and you snapped. It happens to the best of us.”

“But I didn’t just snap.” Dean admits gruffly. The label lays forgotten in pieces between them. “I snapped at _you_.”

“Yeah, well,” Bobby grumbles, leaning back into his chair to stick him with another look. “Just make sure it don’t happen again.”

“It won’t.”

“Okay, then. So what are you still worked up over?”

“I’m not – ” Dean rubs his face with a frustrated noise and after taking one look at the man across from him, sags. There’s just no bullshitting Bobby. He pokes at his burger now, too much of a coward for eye contact. “I guess I just need you to know that I appreciate you. What I said before… look, I know Dad had his reasons back then, but if I ever needed you or if I ever needed help with Sam… you were always there. _Always_. No matter what. You’re still putting up with our shit now and I guess what I want to say is, Dad’s our dad, but you’re… You’re just… You’re a good man, Bobby and uh… and thanks. I just wanted to say thanks.”

It’s a lame finish, but Dean’s never been good with his words. Sam’s always been the one to effortlessly spout out long, chick flick worthy monologues about peace and love and the benefits of communication, so when Dean looks up and sees that Bobby’s eyes are a little red, he’s surprised. To Bobby’s credit though, all he does is mess with his hat and say “it’s about damned time I got a thank you out of you, anyway.” It does nothing to hide how pleased he looks though.

“Uh-huh. Anyway, I better get back to work.”

“Hold on. I’m not done with you yet.”

Dean raises a brow. “I’m the one that came to you, Bobby.”

“And now I’m the one telling you to sit down and shut up. I know your break ain’t over yet, so _sit_.”

Dean complies, looking sheepish as he does.

“Good.” Bobby nods, looking awkward himself. “Now, I know you don’t want to hear this, but Ellen and I have been talkin’ about you.”

“Behind my back? Now that just _hurts_ , Bobby.”

“Shut up, you moron. Look – ” Bobby leans forward, his eyes serious and his frown pulled down with worry. Dean stills, noticing for the first time today how the bags under the old man’s eyes look just a little darker, how his wrinkles sit just a little deeper. Dean’s heart skips a single, painful beat. Bobby looks a little run down himself. How had he not noticed? Is he really that self-centered?

Bobby sighs and takes a sip of his beer, scratching his beard as he collects himself enough to continue. “Now, I can’t afford Stanford and honestly, I don’t know how you can either – no, _shush_ , Dean – ” Dean snaps his mouth shut, all his practiced excuses welling up in his throat, wanting to burst out. “I know you ain’t bartending like you say you are. I’m not an idiot, Dean, and neither are you. We both know bartenders don’t make the kind of money that helps put someone through Stanford, but the way I see it, you come back from wherever you go every night and you come back healthy, so I don’t _wanna_ know. It ain’t my business.”

Dean licks his lips, feeling ashamed of himself for being so transparent and for getting caught. “So, if you’re not wanting to know…” He says carefully, not quite denying that he has his secrets. Bobby’s face is strategically blank. “Then what is this about, Bobby?”

“Well, Ellen and I have both noticed that you’ve been a little tense lately and we both know how hard you’ve been working yourself – don’t think I don’t know about you picking up hours at the Roadhouse every once in a while – _I do_. Anyway, we can’t pay for Stanford, but we can sure as hell give you some time off every once in a while.”

Dean swallows, cheeks warm. “Bobby, I can’t afford to lose any more hours – ”

“ _Paid_ time off, dummy.”

Dean gapes. He never thought he’d hear those words come out of the old man’s mouth. “You can’t be serious – ”

“As serious as a redneck with a shotgun.” Bobby says, his lips twitching into an uneasy smile. “I’m saying every second Monday, you get paid what you normally would for a day’s work, but with zero the labor. Sound fair?”

“Sounds an awful lot like you’re just trying to give me free money.” Dean growls.

“It’s called help, Dean – ”

“I’m not taking your hard earned money, Bobby!”

“Damnit, boy!” Dean flinches when Bobby’s hand comes down hard on his desk. For a second he sees John Winchester, smells the whisky on his breath and prays that Sammy stays asleep, but Bobby’s voice snaps him back out of whatever the hell that just was. “Either you take the paid day, or I give it to Rufus and give your shift to someone else anyway. I’m sick of worrying about you. I need _sleep_ and so does Ellen.”

Dean swallows. The air is tense and quiet and beneath its weight, Dean feels his throat tighten. When both of them keep saying nothing, Dean’s resolve finally crumples. “Fine,” he mutters, feeling gross and guilty, his heart pounding and his palms sweaty. He should have hidden his shit better. He should never have made Bobby or Ellen worry about him in the first place. What if Sam knows something’s up too? A shiver runs up his spine. There’s no room for error in his life, not when he does what he does. “I’ll take the Monday.”

Everything about Bobby softens. “Okay. Good. I’m proud of you – ”

“ _Don’t_.” He sounds pained, but he can’t help it. He doesn’t deserve praise. He hasn’t done anything good or special. “Just don’t, Bobby.”

The old man simply nods. He picks up his burger again – despite the fact that it’s long since turned cold – just as Dean downs the rest of his beer in one go. “Break’s over, kid.”

Dean wastes no time standing up. For once, he’s glad for the distraction and gets out of Bobby’s office as quickly as he can manage.

†

Dean’s still on edge when he gets to the club. He stands outside, steadying himself with slow even breaths, unable to do anything else but glare up at the big neon sign he’s seen so many times before. _The Rack_.

A little over a year ago, when he’d first come to this damned place, he’d been so panicked and desperate. He’d just gotten the news from Sammy – _Stanford_ – and he’d tried so hard to be happy for him, but even with as large as a scholarship as the kid got, they would still owe the school thousands more per semester. There was just no way.

But Dean had heard of this place before, from the years he’d spent looking for various kinds of escapes in seedy dive bars. Strangers had told him of a place that would help him with anything he could ever dream of. And all he would have to do is sell his soul. Figuratively speaking, of course.

Well, Dean figured that after all those years of stealing food for he and Sammy after they’d run out, that he was probably going to hell anyway. Shit, he’d even stolen Christmas presents the few times that Dad hadn’t made it back in time for the holidays and, in the rare occasion that rent money ran out, he’d sometimes even let a drunk stranger use his hands or mouth behind a sketchy bar for a few extra bucks. His soul hadn’t been his in years and so when the strangers had given him a name – _Crowley_ – he’d jumped at the chance. Anything for Sammy, right?

Except, anything for Sammy had led him to Crowley’s office, where he’d been forced to strip down and show off ‘his goods’. Anything for Sammy had led to him sitting in the poncy asshole’s lap, a hand in his hair, as he was petted and asked “ _what’s your price, darling? What’s the price for your soul?_ ” It had led to him saying “ _my little brother’s education_ ” without any hint of hesitation, despite the way his eyes and face had burned in humiliation. (“ _How very noble of you_ ,” the asshole had laughed.)

Anything for Sammy had led to Dean sealing his deal with an agonizing kiss, shared with the crime world’s most douchey player. The kiss had tasted of expensive liquor, and was accompanied by too much tongue and a warning hand on the back of his neck. It had led to him dancing on stage and giving himself away to random men in backrooms and it had led to _Alastair_.

Dean doesn’t realize that he’s been standing in the middle of the sidewalk, practically hyperventilating, until he gets nudged none-too-gently on the shoulder.

“Coming in, handsome?” Meg asks mock sweetly, all piercing eyes and sharp edges. 

Dean glares, but nods. “Yeah. I was just – ”

“I don’t care.” She grins. “Boss is looking for you. He’s getting… _impatient_.”

Dean throws her one last dirty look before he hurries inside. An impatient Crowley is an unforgiving one, but he decides that the bastard can wait a little longer. He slips undetected into the changing rooms and ignores his fellow _colleagues_ for now. Instead, he quickly strips and wiggles his way into his first costume of the night – a pair of almost too-tight leather pants and underneath, lacy green panties. He’s half-way through pulling on his boots when Bella winks at him through her mirror across the room.

“Keeping Crowley waiting, Dean? Not like you to make such a rooky mistake.”

Dean sends her a grin, despite how much he doesn’t like the sneaky bitch. “Was late anyway. Thought the pants could help.”

“Hm. For your sake, I hope they do, darling.”

Dean shrugs, aiming for nonchalant but probably missing his mark by a mile, before he slips back out of the rooms. He steels himself on his way to Crowley’s office and by the time he’s knocking on the door, his back is straight, shoulders held firmly back and his head held high. It’s a silent form of defiance, considering that more often than not, his role in the backrooms is as a sub.

“That better be you, Dean and if it’s not, _piss off and find me that little prat!_ ”

Dean rolls his eyes and opens the door, eyes hard as he pushes his luck. “You called, your highness?”

Crowley is sat at his desk, looking just a level below murderous. Beside him, a man Dean has never seen before is smirking from his own seat, all blonde hair and an immaculate three-piece suit. When Dean catches the mystery man’s eye, that cocky smirk widens and Dean longs to knock that pretentious flat cap off the asshole’s head.

“Dean,” Crowley says, all business and hardly concealed warning. “Sit.”

Dean does, putting his hands on his knees to avoid fidgeting with them. He recognizes the look in Crowley’s eyes and understanding dawns on him. The man – whoever he is – is a new customer and by the looks of him, an important one. If Dean doesn’t behave now, there will be hell to pay for later.

Reluctantly, Dean drops his gaze to the floor and slumps his shoulders, trying his best to make himself look small, just like how his other clients prefer him. 

“ _No._ ”

Dean’s head snaps up at the growl and immediately, the guest is standing and grinning down at him with too much teeth. Dean shudders. Something in his gut tells him not to trust this man. The advice is not too difficult to listen to, considering that his customer base tends to consist of seasoned criminals and shady perverts.

“I don’t want to meet the version of you that you think I want to see. I want to meet you and you are not some common… _pet_.”

“I’m not a pet at all – ” Dean bristles, before snapping his mouth shut. He licks his lips and mentally shakes himself. He’s acting like this hasn’t been his life for the past year, like he’s new to the scene all over again and if the look Crowley’s shooting him is any indication, he’s practically begging for a night of severe punishment. “I mean – I didn’t mean – ”

“Yes you did.” The stranger says, sounding amused. In one fluid movement he closes the space between them and grabs Dean by his chin. Dean meets his gaze and forces himself to remain compliant, as his head is turned one way and then another. The guy doesn’t look it, but he’s impressively strong.

“Dean, this is Mr. Michael Milton. He’s come to watch you perform tonight.”

Dean stays quiet. Subdued. Behaved.

“Is this what you will be wearing on stage tonight?”

Michael leers at him like he’s a meal and suddenly Dean is wishing that he had at least put on the t-shirt that goes along with his costume. “Yes.” Those fingers tighten against Dean’s chin and he swallows back a complaint. The warning is clear. “Yes, _Sir_.”

“Good.” The self-righteous dickwad hums, stepping back out of his space. He looks at Crowley and some sort of understanding seems to pass between them. “I am looking forward to the show.” He says simply.

Crowley dips his head and then Mr. Michael Milton is leaving the room and closing the door behind him. Dean whirls on his boss, who is pouring himself a glass of scotch and muttering to himself.

“Details. Now.” Dean demands, on edge.

“Last I checked, _I_ own _you_ , Squirrel.”

“ _Crowley_.”

The said man leans back into his chair and sips on his drink, a pleased sigh quick to follow. “You know,” he says conversationally with his usual gravelly drawl, peering into his glass as if there would actually be anything of interest in there. “You almost screwed that up for the both of us.”

Dean shifts in his seat, impatient. “Crowley, what’s going on?”

The brit rolls his eyes and leans forward, his thin lips upturned in a way that spells trouble for Dean. “You’re pretty darling, but not much else, so I’ll put this simply for you, shall I? Mr. Michael friggen’ Milton is your ticket out of here, princess. Not straight away of course, but he’ll have you out sooner than you were planning.”

Dean’s heart lodges itself somewhere at the base of his throat. “What are you talking about?”

“I’m talking about _freedom_ , you bumbling imbecile.”

“And Sam?”

“He’ll graduate, just as planned, of course.”

“With what money?”

“Mr. Milton’s of course.”

The office is quiet between them as Dean worries his bottom lip. He considers what Crowley’s shared with him and more importantly, what Crowley hasn’t. A way out? Freedom, but with Sammy’s education still intact? There has to be a catch. For sweet, perfect promises such as these, there always is.

Dean sets his jaw, wearing his suspicion like an armor and scowls at his boss. “Why would you help me? I’m your main performer and your main source of money. It makes no sense that you’d try to get rid of me sooner.”

Crowley flaps his hand, finishing off the rest of his glass. “Let Daddy worry about this, darling. It’d all go way over your head anyway.”

“Crowley – ”

The man’s eyes flash and Dean freezes, remembering exactly who he’s working with. The bastard may look incredibly unassuming and he may play the part of the simple businessman very well, but he is, in fact, dangerous. And he owns Dean.

“I believe you have a stage to be on, sweetheart.”

Dean nods, wrestling himself back into the role of _obedient little whore_. He’s just opened the door when Crowley’s drawl makes him stop again. He looks back and Crowley’s eyes are absolutely _glistening_ , a wicked smirk wrapped around his newly refilled glass.

“And Dean? Do put on a good show. We want Mr. Milton to request you afterwards, don’t we? That is… if you do want what we’ve discussed.”

Dean doesn’t bother answering, but he does slam the office door on his way out for the sheer pleasure of pissing off the King of Hell. Despite his bravado, his stomach is twisting in knots. He’s paid a hefty price for selling the rights of his body and life – ‘ _his soul_ ’ – away, and now, he’s not quite sure what it’s going to cost to get it back. In his experience, it can’t be anything good.

†

Dean, of course, does as he’s told. Just like his Dad had taught him before he’d left him for a new and better life – for a new and better son. Dean was practically raised to follow orders and despite how much of a fuck up he is, it’s what he does best.

He shakes his head clear of his thoughts and lets the sound of the excited crowd around him amp him up instead. There’s no use in torturing himself any more than he has to. These sick bastards around him will happily pay him a pretty penny for the pleasure of doing it themselves.

He gets into position and waits. He’s practiced this routine a thousand times before and he’s confident that he could do it in his sleep. He’s still in his leather pants and boots, but with the addition of a thin, white T that leaves absolutely nothing to the imagination.

Suddenly, the lights come on and the crowd can finally see him. Sitting front and center row is none other than Mr. Michael Milton himself, that dumb flat cap remaining strong and unperturbed on top of his arrogant, rich-boy head. Dean wants to roll his eyes, but instead, puts all his energy into grinning lewdly. The crowd cheers loudly.

Then, the music.

Dean’s swaying his hips to the opening of ‘ _James Dean_ ’ by The Wrecks, one arm thrown up over his head. There are men and women alike cat calling him and when he sends a wink one older lady’s way, she beams and starts to squeal.

_“Imagine for a minute_

_You get up in the morning_

_And get what you want”_

Dean wraps one of his hands around the pole at the center of the stage and slowly, playfully stalks around it. He pauses at the beginning of the next verse.

_“You look good in the mirror_

_Your shirt is full of money_

_You’re getting it on.”_

At the words ‘getting it on’, Dean is leaning back, grinding his hips teasingly into the pole. He’s biting his lower lip, not even trying to conceal his grin as he winks over his shoulder. He arches all the way back until his head nearly touches the stage, the pole an anchor between his legs as he shows off his flexibility. Then he whips back up, not missing the heated look Michael Milton sends his way.

_“Imagine being shallow_

_Thinner than a shadow_

_Thicker than wood.”_

Dean’s hand snakes down his torso, painstakingly slowly, before he pops the button of his leather pants. They’re so tight that they easily stretch open to reveal the green panties hiding underneath. There, he grabs his bulge and thrusts into his hand on time with the beat.

_“Imagine for a minute_

_The way that I’d be living_

_If only I could.”_

At this, Dean struts himself off stage – working his big boots attractively – until he throws himself into Michael Milton’s lap. He straddles those strong, well-toned thighs and licks his lips, knowing that they’re one of his best qualities. The man looks equal parts pleased and thrilled, hands hovering over Dean’s hips as his mouth hangs lightly open with a loss for words. It’s not too long before that mouth is slowly forming into a satisfied smile.

The music hypes up and, with practiced ease, so does Dean.

_“I’m no James Dean_

_Heartthrob, daydream”_

Dean’s mouth is suggestively parted as he grinds down into Mr. Milton’s lap, his hands guiding the other man’s down until they do finally rest on his hips. Michael makes a deep, eager noise.

_“Bad hair, black jeans._

_Not cool. Suits me.”_

Dean’s then bouncing on his lap and messing up his own hair, looking absolutely devilish with mischief as he does so. Michael laughs and those fingers dig into his hips, pulling him back down and in. Dean suppresses the spike of rebellion that quickly rises up within him at being manhandled, especially during a dance. Instead, he curls into the touch.

_For Sammy_ , he thinks.

_“Girls won’t date me,_

_Guys all hate me.”_

Dean grabs his T-shirt at his chest and with ease, rips it in half and throws the scraps somewhere over his head. The crowd screams wildly and without missing a beat, Dean is putting Michael’s hands on his now naked chest. He lets out a breathy sigh when those hands venture _down_ and pinch at one of his nipples.

There’s supposed to be rules against this sort of thing, but this is _The Rack_ and Dean’s trying to rope the rich fool in.

_“Guess that must mean,_

_I’m no James Dean.”_

Dean puts his hands on Michael’s chest and uses the touch to push himself out of the man’s lap. Those eyes track him as he saunters away, looking absolutely starved and predatory. Ignoring the way his body wants to shiver – with distress? – Dean blows a sweet, impish kiss the lusting man’s way and throws himself back on stage.

There, he uses the pole to his advantage and goes through his routine dance. By the time the music’s stopped and he’s hanging upside down, holding on with only the sheer power of his thighs and panting with the effort, he knows Michael Milton has been well and truly caught.

Hook, line and sinker.


	3. Dean

**Notes for the Chapter:**

> Hey, guys! I know I promised you Cas in this chapter, but the characters took a hold of me and made me do things, I swear! I didn't want to not give you Cas though, so I waited until I wrote the next chapter with him in it before I uploaded any new content. The fourth chapter (with Cas) will be uploaded by the end of today, I just need to tweek the writing! So for now, I hope you guys enjoy this one! 
> 
> *Warning* disregard of a safe word, bad dom moments

When Dean returns to the dressing rooms, sweaty and wanting nothing more than to burn all the leather pants in the world, he finds someone lounging in his chair. The room is otherwise empty; Bela, Meg and Kevin probably off somewhere earning their rent money dangling from a pole or with some rich perv’s hand down their pants. Dean, for once, wishes he was with them.

After the whole crapfest that was his meeting with Crowley, he really doesn’t have the energy to deal with Uriel. The bodyguard has never liked him and Dean hasn’t had any other choice but to return the sentiment. The dude’s a raging bag of dicks with the subtlety of a nuclear bomb.

“Well, well, well.” The bag of dicks purrs in his usual condescending baritone. He turns in Dean’s chair and pins him with a smirk. “If it isn’t our filthiest whore.”

Dean snorts and rolls his eyes. The dude is one cat and a pinky to his mouth short of acting like a shitty 90’s super villain. “Alright, Dr. Evil, calm down. What the hell do you want now?”

Uriel stands out of Dean’s chair and presses forward into his space, towering above him and glowering as if he could actually be intimidating. To others he might be, but Dean’s the main whore, thank you very much, and Uriel’s second most important responsibility. Second only to Crowley himself of course.

“Watch your tone with me, _boy_.”

Instead of stepping down as any sensible person would with a wall of solid muscle looming over them, Dean puts on his most infuriating smile and leans right up into Uriel’s space. He takes a moment to relish the way a muscle in the man’s jaw ticks. He has never been any surer in his life that the big lunk is just itching to break his nose. Or his neck. He can’t say he’s never thought the same about him. 

“Why?” Dean asks, all mock charm and hard, challenging eyes. “Did I hurt your feelings, Chuckles? What are you going to do? _Beat me_?” He gives the bodyguard a once over and when he’s sure the guy’s not going to try anything, he steps back into his own space and starts undoing his pants. His gnads are melting in their leather prison, he has a job to do and he doesn’t have time to care about what the damned ogre thinks. “I’m sure Crowley would get a kick out of you trying to explain those bruises.”

Dean’s just undone the button of his pants when a hand like a cannonball shoots out and captures him by his arm, stopping him from undressing. Dean growls and moves to shove the dick off him, but instead finds himself thrown into his own chair. He’s momentarily winded and it’s enough that when he races to scramble back up, Uriel’s already boxed him in with an arm on either side of him. Dean curses and attempts to struggle free, but his chair is wedged against his vanity table and those big, meaty fists are pinning his forearms to the armrests.

Dean knows when he’s lost a fight, but he was raised by John Winchester. When your chances are low, you get lower. He kicks out and hits his mark, but instead of crumpling, Uriel merely grunts and quickly traps the offending leg down with his knee. 

Dean sneers, glaring up at the dick bag above him with all the malice he can muster. Uriel laughs and Dean can’t help but poke at the big, shiny red button that says _“if you want to live, don’t”._

“What, Shrek? You gonna kiss me?”

For a second, Dean really thinks Uriel’s going to hit him. The dude’s beady black eyes light up with rage and those massive hands squeeze his arms so hard that Dean swears he hears his bones creak, but the punch never comes. Instead, the bastard leans in so close that Dean can practically taste what he’s had for dinner.

Dean grits his teeth and leans away as much as he can, upper lip twitching with the effort to not bite a chunk out of the stupid son of a bitch’s face. The warm, wet breath on his cheek tempts him anyway.

“I can’t hurt you with my own hands, boy.” Uriel taunts, voice low and dangerous. "But I can find other ways to make you scream.”

“Shame. I’m not much of a screamer.”

“That’s not what your clients say, _whore_.”

It’s nothing Dean hasn’t heard before. He stays still, knows that Uriel can’t actually hurt him, not unless he wants to be fed to Crowley’s hounds. Eventually, after an intense staring eye contest that has Dean wondering if Uriel is really going to try and kiss him, the bodyguard straightens up and adjusts his suit.

The self-important bastard crosses to the other side of the room quicker than a man of his size should ever be able to. He stops with one hand on the door and turns to grin at Dean. It’s a disturbing sight and Dean wants nothing more than to wipe that smug look off the asshole’s face.

“By the way,” Uriel says languidly, like he hasn’t just risked his own job by threatening the guy he’s supposed to protect. “Don’t change out of those clothes. Kevin Tran will be covering your next number. You and those pants have been requested in _The Cage_.”

The cold laughter that seeks him out, even after Uriel’s closed the door and long since left has Dean swearing and jumping out of his chair. That asshole. Of course he’d come to give Dean the news himself.

_The Cage_.

He curses again and practically throws himself at his vanity mirror, rushing to make himself look presentable.

The Rack, above all else, is a strip club. A classy one run by America’s very own foreign, douchey king of crime, but a strip club none-the-less. However, to certain privileged people, The Rack can be so much more. The place has an abundance of backrooms. Most are seemingly innocent enough; innocent, considering what Crowley’s lackeys have been rumored to get up to.

Most of the rooms are small and only contain a small stage with a pole and a single chair. Those rooms are typically used for private dances. The Cage, however, is a whole other mess and territory.

The Cage is the special, top-secret room where Crowley’s pets go when they really want to start earning what they sought him out for. For Dean, it’s where he goes to meet Alastair, Zachariah, Magnus and sometimes even Abaddon. It’s where he goes to be shoved onto his knees and made to follow his client’s every order, just so Sammy can get the life he deserves.

To be invited to take one of Crowley’s pets into The Cage, one has to be powerful, have considerable social connections and must be trusted to keep everything that transpires in that room an absolute secret. The clients also have to be stupidly rich considering what Crowley will make some poor bastards pay for a singular session. Six sessions a month is all Dean has to dish out in order to stay on top of Sammy’s Stanford bills. More often than not, he’s requested at least twice more than what is strictly necessary and when that does happen, he tucks the extra money away in case he doesn’t get enough requests in the next month.

In Dean’s first year of working under Crowley, he’d been picky with his clients. He’d refused the particularly creepy or unhinged looking pervs that sought him out and as a consequence, there had been a couple of months where he’d only gotten half the requests he’d needed. If Crowley hadn’t agreed to loan him some cash in return for some extra work, Dean would have had to pull Sammy out of college.

It’s precisely the reason why he doesn’t shiv Alastair every time he sees that freak’s sunken, ugly-ass face despite how much he’d really like to. Alastair practically makes up for half his visits and Dean can’t afford to have standards. And really, Crowley would never let someone _actually_ hurt him too bad. The guy’s a gangster, but he runs his show with order and a strict set of rules. He has expectations and if someone doesn’t follow through, then they’re chased down by his boys and fed to his pups. Allegedly.

All of Crowley’s special freaks and pervs are put through a rigorous background check and then forced to sit with him in his office, where he personally explains all of the club’s rules and protocol when dealing with his pets. No lasting damage, no marking up a pet’s face, respect the safe word and absolutely no participating in any activities on the pet’s Taboo List. Of course, there are also cameras scanning every inch of the room that are watched over by Crowley’s security and bodyguards. Other than that, whatever happens in The Cage is free game.

Dean’s gross from sweating up a storm on stage, so he wipes himself down with baby wipes where it’s most needed. He pats the sweat off of his face, fixes his hair and makes sure his pants and boots are all in order. His shirt is obviously beyond saving, so he’ll have to strut into The Cage shirtless. It’s no matter, most of his clients seek him out because of his build anyway.

Compared to the other dancers, Dean’s tall and much more muscular from his life-time spent working on cars. The others are attractive in their own right, but Dean’s clients tend to gravitate toward him because they like the idea of having a big, strong man at their feet, ready to obey their every command. They like feeling in control and holding power over someone that could most likely beat them in a fight.

Zachariah in particular likes to wrangle Dean into skimpy, cheesy girl costumes and make him beg for more orders. Abaddon likes to humiliate him, Magnus treats him like a sacred artifact and Alastair…

Dean shudders. He doesn’t have time for reminiscing. He has a job to do and if Michael can get him out of this mess sooner than what he originally bargained for, then he’s going to aim for employee of the freakin’ month.

†

Dean’s not surprised to see Michael in the room waiting for him when he finally enters The Cage. The man is standing at the farthest wall with his back facing him, admiring the view of all the toys on display there. Unaware that he’s not alone anymore, he gently reaches up to skim his fingers across the surface of a flogger.

Dean grits his teeth and hopes that this man is nothing like Alastair.

“They have to clean everything you touch, by the way.”

Michael turns around, face amused. The asshole looks way too calm in a room filled to the brim with what looks like torture equipment. Then again, he’s the one that gets to play dungeon master, Dean supposes.

“ _Dean_.” He purrs. “It’s good to see you again.”

Michael takes a moment to drink him in, so Dean returns the favor. The guy’s tall – as tall as Dean – with immaculately styled blonde hair and confident, calculating eyes. Even under that pretentious three-piece suit, Dean can tell the man is well-built. He’s handsome. Handsome enough to find himself a good lay if that’s all he desires, despite the annoying, self-righteous way he talks. And the dude’s obviously got money. He’s a triple threat to any chick who’s interested in a hot, rich, powerful guy who dresses like he’s living in the 20’s.

Which begs to question: _why is this dude buying services he could easily get for free?_

The guy has to be into some real twisted _Misery_ crap or something. The thought’s enough to make Dean shift uncomfortably and when Michael’s baby blues track the small, almost undetectable movement, he smiles indulgingly.

“There’s no need to be nervous, Dean. Really. Come here.”

Dean obliges, crossing the room so that he’s standing close enough for Michael to touch him. It’s quiet for a long time while Michael stares him down, but eventually he reaches out to trail his fingers across one of Dean’s cheekbones. He closes his eyes and slowly lets out a small, shaky breath he hadn’t realized he was holding.

Michael chuckles and traces Dean’s lower lip with his thumb.

“Open your eyes, Dean.”

He does. Michael nods approvingly.

“Good. Now, I have rules, Dean, and I expect you to adhere to them while you are under my care. The first rule is that you may only refer to me as ‘Sir’. Do you understand?”

“Yes, Sir.”

“Excellent. Second, I expect you to follow my every command promptly and with zero complaint. Do you understand?”

“Yes, Sir.”

“Third and last of all, I do not tolerate disrespectful or bratty behavior. You are here to serve me and you will do so adequately. If you prove to be a brat or break any of these rules, you will receive punishment. Do you understand?”

Seems easy enough. Dean rolls his shoulders back so that he is standing tall in what others may assume is a militant posture. It’s how his Dad had trained him to stand when receiving orders and despite the raised brow he gets for the small habit, Michael doesn’t seem to feel threatened by it.

“Yes, Sir.”

“I can already tell you were made for me, Dean.” The blonde turns around and makes his way to a nearby chair. When he sits, he spreads his arms out in blatant invitation and winks. “We were interrupted earlier, weren’t we, Dean?”

“Yes, Sir.”

It’s not rocket science to figure out what the guy wants. Dean slips into his ‘good little soldier’ routine like he’s done dozens of times before and follows Michael. When he gets there, he slides a leg over the guy’s lap until he’s straddling him. Beneath him, Dean can feel just how firm and strong the dude is. He’s warm where they touch and suddenly, Dean feels massively underdressed pressed up against what is obviously a very expensive suit. 

The clients get to decide what atmosphere they want to project in The Cage and Michael, of course, has chosen to softly play some old-timey music in the background. It’s sweet and upbeat and makes Dean want to say ridiculous stuff like “ _allow me to take your coat, Mister Milton. I’ll leave it at the door, right along with my father issues. You always get this dolled up for a simple fella like me?”_

Instead, Dean takes a risk he probably literally can’t afford and takes the dumb flat cap off the guy’s head and puts it on his own with a smirk. It must have been a risk worth taking, because in an instant, those sharp, predatory eyes are flashing with hunger. Those hands come to his hips like a parody of earlier and immediately, Dean feels like the mouse that’s been caught by the lion.

His heart is racing, so he puts on his prettiest grin and loops his arms around his client’s neck. “You like what you see, Sir?”

The leather of his pants does nothing to shield the slap that comes down on his ass out of nowhere. Dean jerks with a grunt, only for his chin to be caught by strong, nimble fingers. Michael gives him a pointed, firm look. “Don’t be a brat.”

“Sorry, Sir.”

“I’ll forgive you this once.” Michael whispers, leaning in to nose at his jawline and breathe him in. Dean licks his lips – a nervous tick – and shifts anxiously in the man’s lap. There are teeth grazing at his earlobe, and then, an order. “Give me a show, Dean.”

“Yes, Sir.”

Dean wastes no time moving. With one hand on Michael’s shoulder and the other tilting the cap on his head up playfully, he grinds his ass down into the man’s crotch. It earns him a breathy “ _good boy_ ” and nails dragging down his sides. Dean hisses, arches and enjoys the sting.

But this isn’t about him.

It’s different with the weird 1920s music, but Dean sways his hips lazily to the beat and lets his hands wander down Michael’s chest. When they reach his hips, Dean uses the leverage to slip off the blonde’s lap until he’s kneeling in front of him. There, he puts on his best bedroom eyes and bends down to put a hand on each of Michael’s shins. His hands slowly trail up his legs, Dean’s mouth following their path with gentle, open mouthed kisses. He paused to bite carefully into the meat of Michael’s inner thigh, right above his knee, when his hands make it to his upper thighs.

It earns him a small, appreciative moan and a hand in his hair.

Dean looks up from under his lashes, unable to stop the devilish grin that stretches his full, pink lips. He relishes in the way Michael’s eyes are almost completely black with lust, and feeling brave, he strokes his hands up and down each thigh before allowing them to settle on each knee. He pauses to make sure he has Michael’s full attention, before he winks wickedly and thrusts the man’s legs apart as though he were actually the one in charge.

With a sigh and his hands still on Michael’s knees, he leans in until he’s between those legs and his chest is flush against the dude’s abdomen. When he feels the guy’s obvious problem in his pants, he chuckles and dips down to mouth at his hip.

Dean doesn’t expect the hand in his hair to sharply pull him back.

With a startled growl, Dean arches to try and alleviate some of the sting, but it only encourages Michael to wrap his other hand around his throat in warning. Dean goes rigid, watching with wide eyes as Michael leans in as if to kiss him. No kiss comes. Instead, his breath hitches as he feels teeth sink gently into the flesh of his cheek. It’s not enough to hurt, but enough to make him freeze obediently.

When Michael speaks, his voice is low and threatening.

“Didn’t I tell you not to be a brat?”

“You may have mentioned it in passing, yeah.”

Michael laughs, incredulous. “You can’t help yourself, can you?” He’s smiling, looking at Dean like he’s a cross between something baffling and something he’s waited a very long time for. Dean tries not to be too creeped out by it.

“Stand up, Dean. We’re going to play a game.”

It sounds far too much like something Alastair would say, but Dean moves to obey anyway. Only, before he can even stand, the hand in his hair snaps him back down onto his knees and it _hurts_. Against his better judgement, he glares up at the bastard leaning over him. Michael doesn’t look phased at all.

“Tell me, Dean. Are you trying to earn a punishment, or are you really so spacious upstairs that you’ve already forgotten all of the rules I’ve given you?” When Dean says nothing, Michael rolls his eyes and tugs even harder. Dean swallows his wince. “I gave you an _order_ , Dean. What do you say?”

“I say ‘yes, Sir’.”

“So, why didn’t you?”

Dean licks his lips and refuses to look away. “It won’t happen again, Sir.”

“Hm. Crowley said you’d be trouble to start with. Should I find a better sub, Dean?”

Dean grits his teeth. He’s not going to beg the bastard to stay, even if the dude can apparently get him out of this shithole sooner. But, this is for Sammy. This is Sam’s one shot at a better life where he doesn’t turn out like his loser big brother or alcoholic father. He curses the kid’s big brain and lowers his gaze dutifully. _For Sammy_. “No, Sir.” He says softly, forcing the fight to leave his body. His shoulders slump and he bows his head down further. “I’ll behave.”

When this Stanford thing is all said and done, Dean better be mooching off the kid’s six figures until he’s nothing but ash in the ground. He’s freakin’ earned it.

Dean remains still while the hand in his hair starts carding through it. It’s soothing and tender and Dean instantly hates it. After a long moment of what he guesses is Michael considering whether to continue the session or not, the hand falls away. “Stand up, Dean.”

“Yes, Sir.”

Dean does as he’s told, eyes still trained on the ground. Michael hums happily.

“As I said before, we’re going to play a game, Dean. I’d like to get to know you. For each question asked, you will be given a choice as to whether or not you would like to answer. If you do answer, you will be rewarded. If you do not answer, you will be punished. Do you understand, Dean?”

So he gets to choose whether he’s rewarded or punished? “Yes, Sir.”

“Strip out of those pants. Fold them, put them down neatly and keep those lovely panties on. When you’re done, lay over my lap. Understood?”

“Yes, Sir.”

Dean could cry tears of relief when he finally gets to take those damned pants off. He’ll never complain about the corsets again, so long as he never has to wear those damned, too tight, leather pants ever, ever again. He folds them neatly and then puts them on the ground next to his boots. Doing as he was told, he approaches Michael and then lowers himself so that he’s laying over the dude’s lap. His cheeks warm when he’s reminded by the feel of expensive fabric beneath him just how nicely dressed Michael is compared to him, wearing nothing but his green, lacy panties.

He forces himself to breathe when a hand sooths over his ass.

“Are you ready?”

“Yes, Sir,”

“Let’s begin with something easy, shall we? What’s your full name?”

“Dean Smith.”

Dean flushes when Michael laughs so hard that it shakes the both of them. “Cute, Dean. Really.”

He’s not sure whether he’s going to be rewarded or punished until he hears a cap pop. He tenses when his panties are tugged over just the littlest amount, before a cold, wet finger starts circling at his hole. The finger does nothing but tease the area, slowly and carefully. Michael’s other hand is warm against his back where it rubs comforting circles, fingers massaging at his muscles approvingly. Dean supposes this is the reward and forces himself to relax.

“Next question, Dean _Smith_.” The bastard chuckles again. “How old are you?”

“Twenty-four, Sir.”

The finger gently presses in, just the tip.

Is this what the guy gets off on? Twenty questions? Weird kink but Dean’s been through worse.

“What’s your favorite food?”

_Easy_. “Pie, Sir.” The finger in his ass presses in further and Dean lets out a small moan. It’s slowly thrusting in and out when Michael asks, “cherry or apple?”

“Both, but if I had to choose, apple, Sir.”

The hand on Dean’s back disappears and then he can hear more lube being squeezed out. It’s cold when it hits his ass, but then Michael is scooping it up and pressing in another finger. He’s moving agonizingly slow, scissoring him with the utmost care and Dean wants to snap at him to get on with it already. It feels good and he can’t really remember a time when another client pleasured him without being a jerk about it.

“What kind of music do you like, Dean?”

“Classic rock, Sir – _ah!”_

Dean swears as those fingers keep hooking into his prostate. He wraps his hands around the legs of the chair they’re on and hangs his head low, biting his lip. His legs are shaking with the effort to stay still in Michael’s lap and the bastard must notice, because he’s bending down to kiss at the nape of Dean’s neck.

“You’re doing _so well_ , pet. Look at how beautiful you are, being so good for me.”

Dean lets out a small gasp and then those fingers are withdrawing just enough so that they can resume their gentle thrusting.

“Who is your favorite musician?

“Led Zeppelin, Sir.”

Finally, a third finger slips in. It doesn’t even burn because of how cautious Michael has been with him. He speeds up the thrusts and then Dean is writhing in his lap, face and chest hot with both embarrassment and pleasure. If the dude’s not careful, he’s going to need to dry clean his suit.

“Favorite song?”

“Ramble on, Sir – _shit!”_

The bastard’s thrusting harder now, putting his whole arm into it and aiming for his prostate each time. Dean whines when Michael’s other hand swats his ass.

“ _Language_ , Dean.”

“S-Sorry, Sir!”

All three fingers spread out and Dean’s moaning, unaware that he’s moving back to meet each thrust. The hand that spanked him runs through his hair.

“Do you have any siblings?”

Dean freezes and so do all of Michael’s ministrations. He withdraws his fingers and leaves Dean feeling empty, but he can’t find it in himself to care. There’s absolutely no way that he’s bringing Sammy into any of this, small talk be damned. He doesn’t know what to say or do, so he does nothing but stay quiet.

“Dean?”

When he doesn’t move to answer, Michael sighs.

“It’s your choice, pet.”

Dean grunts when he’s spanked – not just once, but five times in quick succession. The bastard doesn’t hold back either, giving each hit his all. Dean tightens his hold on the chair legs into fists, taking extra care not to make any more noise. When Michael’s done, he drags his nails down the redness of Dean’s ass and it burns enough that he hisses.

“I’m surprised that it’s that particular question that alarmed you. Give me your hands, Dean.”

Dean does, folding them behind his back as though they were tied. His stomach knots when Michael wraps a hand around his wrists and pins them down. The other hand returns to his ass and sits there, cool against the burn.

“Tell me, Dean. Why are you here? What deal did you make with Crowley?”

_Seriously?_

Dean turns his head the best he can, but he can’t get a good look at the bastard’s face. There’s no way the dude just asked that question. He’s pretty sure there are rules against clients asking about that kind of thing and even if there wasn’t any, there’s no way Dean would tell him.

“I’m not going to tell you that.” He says instead, wary. The atmosphere has changed and Dean doesn’t know what to make of it. He just knows that his gut feels tight and he can’t get himself to relax.

“I insist that you do.”

“Look,” Dean snaps; anxious and feeling way too vulnerable being practically naked on the dude’s lap. “Last time I checked, that’s none of your business, Nancy Drew.”

He cries out when the next blow comes down and catches him on the upper thigh, right below the cheek. He expects to just get the other four spanks, but instead, they keep coming. By the time Michael stops, Dean has long since lost count and he’s struggling against the hand pinning his wrists down. His entire ass feels like it’s on fire and he’s gasping past the pain. At some point during the onslaught, Michael had managed to twist his torso so that he’s now leaning over him, his elbow tight against Dean’s side so that he’s boxed in against him with no room to break free.

“What the hell?” Dean shouts, trying his best to escape the hold. He growls and thrashes harder, but the bastard’s got him. “Get off!”

“Who do you belong to?”

“The fucking government, now let me go!” Michael doesn’t budge an inch and Dean only panics more. His chest feels tight, his breathing coming out louder and more ragged. He kicks his legs but it’s no use. “Impala! I’ve safe worded, now get the hell off me!”

He cries out when Michael throws him to the ground. His chest collides painfully with the concrete below, his head soon to follow with a much too loud crack. Dazed, Dean groans and manages to get his hands under him, but a kick to his side sends him sprawling back down.

There’s a pressure on his head and when he blinks his eyes open, he realizes that an expensive oxford shoe is pressing the side of his face into the floor.

“Fuck off.” He rasps, head and body throbbing.

“Who do you belong to, Dean?”

“Revisit my earlier statement.”

He shouts when that shoe twists down into his face like he’s a cigarette butt. His hand scrambles up and finds an ankle. He pulls, but his hand is quickly snatched away. Where the fuck are the bodyguards that are supposed to stop his face from getting messed up? Where the fuck were they when he safe worded?

“Who owns you, Dean?”

He stays quiet. He hears the safety of a gun.

His blood turns cold and he doesn’t dare breathe.

_No._

They check for weapons at the door.

There’s no way that Crowley would let this shit go down.

“ _Dean_.”

He has to. He has to for Sammy.

“You. I belong to you.”

“Good boy.” Michael releases him and steps back. Instantly, Dean jumps up, head buzzing and spinning, but ready to fight anyway. The blonde rolls his eyes, hands held up in mock surrender. Not a hair out of place.

“Calm down. I’m leaving.”

Dean swallows. Glares. “For forever. They won’t let you back in after this.”

Michael grins, slow and sure. Dean tightens his jaw, hardens his glare. He hopes the bastard doesn’t see how his hands are shaking.

“Oh, but they will. I’m more powerful than you can imagine, Dean and as you said, _you belong to me now_.”

Michael leaves the room swiftly and then Dean’s left standing in the middle; panting, eyes wide, ass wet with lube and nothing but the crappy 20s music to keep him company. He shudders and rushes to put his pants and boots back on.

He doesn’t spare The Cage a backwards glance when he leaves. He doesn’t think about how he must look, bruised and shaken, and he doesn’t think about what it meant when none of the bodyguards showed up to do their damned jobs. He definitely doesn’t think about what Michael meant when he said that he owns him now.

Dean lets all of whatever he’s feeling turn into anger. It’s with that anger that he charges into Crowley’s office.


	4. Dean

**Notes for the Chapter:**

> Number four is here guys! AND SO IS CAS! Yes! Finally! 
> 
> Just as an aside, thank you all for the continuous support you have shown me. Your comments and kudos and questions have kept me motivated! I appreciate all of you so very much! <3
> 
> Also, in case anyone was wondering, I did in fact switch to using these bad boys (") for dialogue. I usually use these sleek fellas (') in my typical writing, but I felt like they don't look as nice in this format. Hope that doesn't mess with you guys too much!
> 
> Thank you for reading and as always, I love hearing from you guys! I hope you enjoy! =)

“Ah, Dean.” Crowley says, a contract in his hand. Dean’s standing in the middle of his office, door slammed behind him, arms crossed and looking like he may just try to kill the King of Crime. “You look smashingly disheveled. Play house, did you?”

Dean snarls. “What the hell was that, Crowley?”

“A greeting. A rather polite one might I add.”

“I’m not playing around, you poncy dick. That asshat you paired me up with pulled a gun on me and your boys did _nothing_ to stop it!”

Crowley raises a brow at the finger Dean jabs in his direction. “A gun?” He asks mildly. He looks Dean over, sees the impressive bruise forming on his side and continues to look bored. “Do tell me, Squirrel. Did he shoot his load in you?”

“ _Crowley_.”

The gangster tuts and leans back in his chair, taking a long sip of his whiskey. “That’s your problem, Dean. No taste for good humor.” When Dean just continues to glare at him, looking absolutely livid, Crowley rolls his eyes. “As much as I love the twinkle of bloodlust in your eyes, it’s getting old. Take a seat, pet. Daddy will tell you everything.”

He wants to snap at Crowley and tell him to quit it with the ‘daddy’ shit, but he knows it will only encourage him to do it more. Instead, he takes a seat, looking no less angry. He watches as Crowley casually collects another glass from one of his drawers and fills it half-way with his own very expensive whiskey. When he offers it to Dean, he takes it cautiously.

“Twelve years old and absolutely drug free. Believe me, I wouldn’t waste any of the valuable stuff on you.”

Dean scowls and downs the entire glass like a shot. Crowley looks appalled.

“You’re not a very appreciative one, are you, pet? Where I come from, we savor a good drink.”

“I’d _appreciate_ you telling me what the hell all that shit with _Judge Dredd_ back there was all about.” He growls, voice gravelly from the burn in his throat. It’s a welcomed feeling compared to the burn of his ass each time he moves in his seat or the throb of his head from where it had hit the floor earlier.

Crowley pauses and considers him seriously. After some time and a few more sips of whiskey, he says “If I were to tell you exactly what is going on, I’d have to feed you to my hounds. All _you_ need to know is that Michael Milton is a very important man and that it’s your job to keep him happy.”

“Like hell it is! I’m not meeting with him again, Crowley.”

“Why? Because he brought a gun to a cock fight?”

“Shut up.” He says, ears burning. “It’s not happening, period. I don’t care if he can get me out early. I won’t see him again.”

“Yes you will.” The brit says simply, lacing his fingers together and smiling at him deviously. “Unless, of course, you’re prepared to tell little Sammy that he can’t go to his big boy school anymore?”

Dean feels like he’s been punched in the chest. He grits his teeth and spits out “ _what?”_

“Like I said before, Squirrel: Michael Milton is your ticket out of here. I need him for something _super top secret_ , shall we say, and I need _you_ to make him want to stay. If you can manage to do your job and keep him around long enough for me to do my thing, I’ll free you. Little brother’s school all paid for and no more late night booty calls for you. That has to be easy for even you to understand, right, pet?”

“And…” Dean licks his lips and fiddles with the glass still in his hands. He sits taller, wishing that he at least had the hindsight to change or even put on a damned t-shirt. He’s hyper aware of how wet it feels in the back of his pants and he refuses to let himself cringe at the thought of how the lube got there in the first place. “And if I say no – ”

“Then I cut your contract early. No school for Sammy, no more money and _you_? Well, I’d feed you to the hounds, but I think that you’d prefer that over living with knowing that _you_ were the one to ruin little Sammy’s life.”

“He broke every rule, Crowley. You can’t do this.”

“How you’re related to a man going to Stanford is _beyond_ me, Barbie.” Crowley grouses. He leans forward and Dean instinctively leans back. With narrowed eyes, Crowley stares at him, until eventually he huffs out a small, knowing laugh and settles back in his chair. “You’ll work with him, Dean. I mean, isn’t that your thing? Self-sacrifice and everything nice?”

Dean looks away and swallows, knowing that the bastard’s not wrong. He’s being incredibly selfish. Is he really willing to give up Sammy’s whole future because of _this_? A gun? Shit, it’s not like it’s the first time he’s been held at gun-point before. And the bruise? John Winchester’s given him much worse on a good day.

“I mean really, what are you without that boy? You’re so dependent on his success that I actually feel sorry for you.” Crowley continues, picking at imaginary fluff on his suit. “You know you’re pathetic when I feel bad for someone other than me.”

Dean’s head snaps up and he sneers. “Shut up, Crowley.”

“Of course you’ll do anything for your little brother. Because if he fails, then that means that _you_ failed _him_.”

“I mean it – ”

“And if Sam sees just how bottom of the barrel you really are, then maybe he’ll decide to just never come back – ”

“ _Crowley_ – ”

“And if he does graduate? What would a fancy, accomplished lawyer want with an uneducated, borderline alcoholic _whore_?”

“ _I SAID SHUT UP!”_

Dean stands so quickly that his chair flies back, the glass that was in his hand shattering as it hits the wall beside them. He stares at the shards, feels tears stinging in his eyes and hears footsteps coming from somewhere behind him. He just stands there and pants, feeling so much like the broken glass. Feeling so angry and resentful that _this is his life_. That his best is almost never good enough and that he has to choose between playing pet to some power hungry dick with a gun or his little brother’s education.

His eyes slip closed and a single tear makes its way past his freckles.

“Well. That was a rousing show of emotion.” Crowley comments, deadpan. He’s right behind Dean, patting his back. “Now that we finally got that out of your system, can we get back to bloody work?”

Dean breaths in deeply and reaches up with a single hand to wipe his face dry. When he turns to glare at Crowley – his usual mask of default pissed off slipped back on – his boss is smiling at him coolly, hands in his pockets like Dean doesn’t want to strangle him right then and there.

“That is… you _are_ still working for me, correct?”

He imagines Sammy sitting at his favorite desk in class – because that dork _would_ have a favorite desk. He sees that Ruby girl right there beside him and he sees them laughing together, sees Sam happier than he’s ever been in his life before. He sees him making his dreams come true. He knows that Sam is going to become something, something _more_ than what he already is. 

Then, he imagines calling Sam. He imagines telling him that he has to come home because his big brother’s fucked up just like he always does. He sees Sam having to leave his perfect, normal life behind to work at The Roadhouse. He sees him become just like their dad, because Dean will never say it, but Sam’s always been more like their old man anyway. He knows Sam will never want to talk to him again and, really, _who would blame him?_

“ _Dean_.” Crowley sing songs. “You are still working for me, yes?”

If only Mom had just lived…

Dean steels himself – brings himself to full height – and nods. “Yeah. I still work for you.”

“Good. Now that you’ve wasted both of our time, _get back to work!”_

Dean's glare intensifies. “When this is all said and done, Crowley, I’m going to shove a knife so far down your throat – ”

“Don’t make promises you can’t keep, darling. Now, be a dear and fetch Kevin for me. I do love torturing the little lad.”

†

Monday morning finally comes around and so does Benny, shaking him roughly at seven in the morning. “Brother,” he says with panic in his voice. “Ain’t you supposed to be workin’?”

Dean groans and tosses his pillow at his friend. He then frowns, because he misses his pillow. “Day off.”

“ _Day off_ – ” Benny bends down to pick up the pillow and then stares at him incredulously. “Brother, I ain’t ever seen you take a day off in my life.”

Dean would laugh at the look on his friend’s face if he weren’t so bone tired and hurting everywhere. “Bobby wanted me to take the day, I told him no, so we comprised and I’m taking the day. We done?”

Benny blinks and then laughs. “Is that so? Well, then,” he tosses the pillow back to Dean and winks. “Who am I to disturb small miracles?”

“Fuck you.”

“In another life, brother. Shall I tuck you in?”

“I’m a grown ass man, Benny.”

“That’s a yes, then.”

The big man swoops down and does just that, taking extra care to tuck the edges of his blanket under him just right. Dean rolls his eyes and grumbles like he’s supposed to, but in all truth, it actually feels kinda nice. He kicks the big bear when he kisses him on his forehead though.

“That’s enough!”

“Alrigh’. I’ll leave you to your beauty sleep now, princess.”

“Again. Fuck you.”

“Ask me one more time and I might just say yes.” Benny laughs, deep and familiar and sounding like home. When he leaves, he closes the door gently behind him, but it doesn’t matter because Dean’s already out cold. 

†

The next time Dean wakes, it’s to the smell of bacon. He stumbles out of bed, hair sticking up at odd ends and mouth stretched open in a wide yawn. He hisses when his boxers brush the wrong way against his ass and when he looks down, he sees a big black bruise with yellow edges on his side. He pokes at it and grimaces. When he dresses, he takes extra care to make sure that all blemishes are hidden. Benny doesn’t need to see that crap.

Next, he looks into the camera on his phone. Thankfully, his face is bruise free. He grabs his blanket and walks into the kitchen, wearing it like a cape.

“Mornin’, Sleeping Beauty.” Benny chuckles. “Thought you’d want some lunch.”

“Lunch?” Dean squints and looks at the microwave. The numbers _12:48_ stare back at him. “Shit,” he says, with feeling.

Benny hums in agreement. “I figured you needed the shut eye. Hope you didn’t need to be anywhere?”

“Nah. Nah, you’re good, man.” Dean slides onto a stool at the kitchen island, content to watch Benny do his thing. He ignores the pain that flares on his backside that sitting brings him and instead, leans forward to peak at what’s in the pan. “Are those the fancy little potatoes? I _love_ those things.”

“They’re called roasted potatoes, cher. Coffee?”

Dean moans “Jesus Christ, _yes_ ” and then Benny’s pressing a hot mug into his hands. He takes a sip, burns his tongue and moans again anyway. “Where the hell did I find you again?”

“If I recall, I found _you_ , brother.” Benny chuckles and does some cool flippy shit with his pan. “The real question is, how on God’s green Earth do you manage to get up so early in the morning? You’re the least morning person I know."

Dean nods, understanding completely, but unwilling to pull his mouth away from his coffee long enough to answer. Benny snorts.

Dean’s just finished inhaling his coffee when his friend slides a plate in front of him. It’s overflowing with _roasted_ potatoes, bacon, eggs, fruit and sausage. He looks up, maybe with tears in his eyes, and says “ _thank you_ ” like a prayer.

Benny looks mildly concerned for him.

“I never get to spoil you like this. When we have dinner, you’re always in a rush. I’m just happy to see you taking time for yourself, even if you were forced into doing it.”

“Yeah, well,” Dean says, spearing a potato with his fork and plopping it into his mouth. He closes his eyes and moans around the bite. Spice and oil and _goodness_ explodes on his tongue. “It’s gonna become a regular thing. Bobby’s giving me every second Monday off from now on. He says it’s _paid time off_ , but…”

“But it just feels like free money?”

Dean looks up and nods.

Benny smiles and takes a bite out of his own breakfast. “I think it’s a break you deserve, cher. You work yourself so hard these days, I don’t think you realize how much you look like a zombie. The old man just cares ‘bout ya.”

“Yeah, but – ”

“He’s family, Dean. This is what family does. Don’t tell me you wouldn’t do the exact same for Sam if he was in your position.”

Dean bristles. “He’ll never be in my position.”

“Yeah,” Benny says, leering at him sharply. “Because you won’t let the kid get a job.”

“He’s in school, Benny. He should be studying and chasing tail. Besides, I work so he doesn’t have to. I’m doing this so the kid can have a life that isn’t just wasting away in a motel room, watching Scooby-Doo reruns and drinking at the local dives.”

“I thought you liked Scooby-Doo.”

Dean snort laughs around a forkful of eggs. “Ha. Yeah, I do. I’d take a bullet for that dog.”

Benny pokes around his plate, making a small noise in the back of his throat. Dean’s in the middle of remembering a particularly funny episode when his friend draws him back into the real world with his sweet, Cajun accent. “So, what about _your_ life, Dean?” 

Dean pauses, cheeks puffed out with potatoes.

Benny smiles at him fondly. “This can’t be all on you, brother. You know, if you let Sam get a job, you might just be able to drop a few shifts and then, hell, maybe you could actually do something for you.”

Dean gulps his mouthful down with a little struggle and then narrows his eyes. “We’ve talked about this, Benny.”

Benny shrugs. “It’s just, I’ve heard you talk plenty about your brother’s dreams, but I’ve never once heard you mention yours. Have you even _thought_ about your dreams, Dean?”

Dean drops his fork onto his plate and continues to stare. Benny’s beaming at him innocently, his big, sky-blue eyes bright with mischief.

“You lured me in with food. I felt safe. I trusted you. This was a trap all along.”

“Aw, brother, don’t be like that.”

Dean huffs. “It’s my day off. I’d like to enjoy it without being ambushed into having an existential crisis, if that’s okay with you.”

“You’re the princess, cher.” Benny says, going back to his plate. Dean nods and does the same, grumbling “yeah. _I am_ the princess” under his breath.

They finish their meals together in companionable silence. Afterwards, Dean does the dishes despite Benny’s protests and then they sit on the couch, happy to just watch the game and catch up with each other.

They drink sodas because Dean refuses to drink in front of his best friend – _ever_ – and when Benny takes him by the shoulder and pulls him in to grind a fist playfully against his ribs, Dean hides his wince. They wrestle for a little while, falling off the couch and going so far as to roll around on the floor. They only stop when a phone starts to go off.

“Not me.” Benny says, eyebrows raised as he hovers over him.

Dean scrambles out from beneath his best friend and races to his phone, answering just in time.

“Hey, Dean. You sound really out of breath. Are you okay?”

“Sammy! How did things go with that girl? – _Ruby_. I got it. How did it go with _Ruby_?”

Dean sends a wave Benny’s way and steps outside. “You were right about the whole thing! It worked and we have a date coming up this Friday!” Sam sounds so awed and grateful. “Thank you so much, Dean. I wouldn’t have gotten this far without you.”

The older Winchester tries to ignore the way his heart pangs. Sammy wouldn’t sound so awed if he knew just how badly he’d almost messed up life for him the night before. He’d been so stupidly reckless, risking his little brother’s entire future just because he got pushed around a bit. “It’s no problem, Sammy.” He says past his guilt.

“No, Dean, I mean it. Thank you for – not just for Ruby, but, you know, uh, for everything you do and – ”

“Alright, Samantha.” Dean mutters, unable to help his smile. “Now tell me more about this Ruby chick. Is she hot? How was the party?”

Dean putters around the house, listening to his little brother rattle on and on animatedly about the night he had. At one point, Benny leaves for work and Sammy’s still gushing. The only thing that could make this moment any better is if Sam were actually in front of him, suffocating him in one of his big, gangly hugs. But otherwise, this is perfect. Better than perfect; this is the happiest Sam has sounded in a long time.

They talk for a long time. Dean rolls his eyes in all the right places even though Sam can’t see him and yells “I told you so!” when Sam sheepishly tells him that “Ruby punched me on the shoulder when I asked her out. She said she’d given up all hope that it would ever happen”. By the time the call’s ended, Dean’s buzzing with an energy he hasn’t had since he was a teenager.

It’s enough that he drags his good mood outside to Baby, where he starts tinkering with her. He runs his hands up her flanks and whispers lovingly to her, careful to dip his washcloth into her every crevice. When she’s all tuned up and purring prettily, they make their way to the Roadhouse, Metallica bursting from her speakers. Dean pointedly doesn’t play any Zeppelin.

He’s singing along terribly, the wind whipping his hair in every direction. This is his first day off since, well, _ever_ , and he supposes that it’s cause enough for celebration. If the way Baby’s roaring around him is anything to go by, Dean thinks that she might just agree too.

†

“Dean-o!”

Dean pretends to look horrified as Ash jogs up to him, a dopey grin plastered to his face. “They still let you show your mullet at this joint?”

“The mullet is what makes them want me to stay.” Ash winks, pulling him in for a bro hug. “What’s up, Winchester? Don’t usually see you at this time. Or, like, _ever_ these days.”

“Day off,” he shrugs with a grin. “You know how it is.”

“I abso-fucking-lutely _do_. Beer?”

“Yeah, man.”

“Jo, get this tall drink of water here an even taller pitcher of beer!”

Jo flips them off from the bar. “You work for me, shithead!”

“Actually,” Ellen says, coming in from the back with a stern look on her face. “You both work for me, so stop messing around!”

“Shit, my man. You know how it is.” Ash says with a shimmy.

“I abso-fucking-lutely _do_.” Dean chuckles, clapping him on the back and following him to the bar. Once there, Ellen immediately engulfs him in a hug that reminds him of his mother. Jo punches his shoulder.

“You haven’t been showing yourself around these parts enough, kiddo.” Ellen scorns accusingly. “Haven’t been cheating on us, have you?”

“Nah, Ellen.” Dean says, feeling more peaceful than he has in a very long time. He’s missed this place and he’s missed these people. “Work’s just been kicking my ass, that’s all.”

Ellen gives him a knowing look. “And you spoke with Bobby?”

Dean looks down at his shoes, ears hot. “Yeah,” he says shortly. “I spoke with Bobby.”

“And?”

He rolls his eyes. “And I got the message loud and clear. Happy?”

Ellen laughs and slugs his shoulder. Mother like daughter. “Yeah, kiddo. Actually I am.”

They catch up over their beers, but eventually as time stretches on and people keep filtering in they all have to get back to work, leaving Dean to sit alone contentedly on his stool. He’s enjoying the general atmosphere, soaking in the warm wood rafters and quirky decorations that he’s missed so dearly, when some guy in a worn trench coat sits down next to him.

“Do you frequent this place often?”

Dean scrunches his face up and looks at the guy with his best ‘ _are you serious?_ ’ face, only to be startled by how truly handsome the dude next to him is. He may be dressed like a dweeby tax accountant, but he’s _hot_. His dark hair screams bed head and those big, soft eyes are absolutely killer. Are eyes even supposed to be that blue?

He’s gotta be the most angelic looking dweeby tax account Dean’s ever laid eyes on.

The man frowns. “I’ve never been here before. ‘ _Roadhouses’_ …” the dude uses honest to God finger quotes. And _that_ _voice_. “They’re uh, not typically ‘ _my thing_ ’, I’m afraid.” He’s smiling sheepishly, looking so endearingly out of place that Dean’s heart starts to jackrabbit.

Dean licks his lips and then takes a sip of his beer, his mouth suddenly very dry. He clears his throat and then looks at the guy again. He’s wondering if he might have been a nun in his past life to have the good fortune of even catching a glimpse of this dude, when he realizes that he hasn’t even answered him yet. _Crap_. “Why – ” His voice cracks and he coughs, cheeks warm. “Then, uh, why are you here then?”

“Oh. I’m meeting someone.”

 _Of course._ Dean deflates and takes another sip of his beer.

“My brother, actually. He’s been wanting to visit this place for a while. He hears they make very good pie here.”

Dean perks up again immediately. “They do make really good pie here! Everything’s good, but the apple’s always a classic and – ” He halts mid-rant when he catches the amused expression that the man shoots him. He scratches his forearm anxiously and turns back around, mentally slapping himself. “I mean, yeah. It’s really good. But all pie is good.”

“Indeed.” The guy says, not looking annoyed in the least. He starts turning in his seat, seemingly taking in their soundings. The Roadhouse ain’t exactly _The Ritz_ , but Ellen keeps the joint clean and it’s home to many a good hearted drunkard. Even the few iffy ones are well loved. It’s classy for what it is and more importantly, it feels like coming home after a very long day. Every single time.

The strange man turns back to Dean, holding out his hand with an easy smile. “I’m Castiel, by the way.” He says, and God, his parents must have really wanted him to grow up being bullied. _Castiel?_ What the hell kind of name is that? “You are?”

“Dean,” he hastens, taking a hold of Castiel – fuck it – _Cas’_ hand. It’s warm and callused to the touch, but Dean likes it anyway.

Instead of withdrawing as any other normal person would under similar circumstances, Cas lays his other hand over their joined ones and leans forward with the most earnest gaze Dean has ever seen in his life. It’s so intense that he thinks he might just start to drown in those big ocean blues. “It’s _very_ nice to meet you, Dean.”

“Yeah, uh… you too, man.”

They pull apart and then Dean’s downing the rest of his beer. Jo comes around to serve them, a shit eating grin on her face.

“Another beer?” She asks sweetly.

Dean nods, feeling uncharacteristically nervous. “Yeah, and uh, one for my buddy Cas here, too.”

“Coming right up.” She winks, shuffling off to go grab their order.

She delivers the beers with one last teasing face that Dean hopes Cas doesn’t notice, then leaves to go wipe down some tables. In the sudden silence, Dean starts fiddling with the label of his beer. He’s peeled half of it off, unsuccessfully ignoring the hole his new ‘buddy’ Cas has been staring into the side of his head, when the dude finally speaks up again.

“That was very kind of you.”

“Yeah, well,” Dean clears his throat. “I have my moments.”

It gets quiet for a little while again and Dean’s just beginning to tense up when he sees Cas’ beer sneak into his line of vision and clink against his own bottle. He blinks. “ _Cheers_.” The nerdy little angel dude says, like an alien trying and failing to sound like a human. It’s so bizarre and random that Dean can’t help the laugh that tears out of him. When he looks over, Castiel is positively _beaming_.

He shakes his head and nudges the dude’s shoulder with his own. “You’re alright, Cas.”

The dude ducks his head, looking shy. “You call me ‘Cas’.”

“Oh, I didn’t mean – ”

“No,” the brunette says, looking pleased. “I like it. Really.”

Dean swallows and nods, trying to look nonchalant. “Cool. Good.”

They finish their beers together and then Cas is buying them their next round. By the time they’ve finished their second drinks the initial tension has melted away entirely, and even though the dude is definitely weird, Dean finds that he can’t help but like him. He's got a peculiar ease about him, a comfort that Dean doesn’t usually find in people he’s just met, or at least hasn’t known for a few years. Plus, the dude talks about the craziest, most outlandish things.

He’s in the middle of explaining to Dean that bumble bees sometimes take naps inside of flowers when the bar doors swing open and someone hollers “ _Cassie!_ ”

Cas looks as disappointed as Dean feels.

“That would be my brother Gabriel.” He says, smiling apologetically. “It was very nice speaking with you, Dean.”

“Yeah,” Dean murmurs, standing when Cas does. He rubs the back of his neck and summons all the courage he has. He really hopes he hasn’t read this wrong. “Look, uh, Cas, before you go… maybe we could do this again sometime?”

He blinks. “You want to drink again?”

Dean curls in on himself, feeling mortified. _Of course he read this wrong_. “Or lunch, or whatever.” He mutters softly. “I mean, you don’t have to if you don’t wanna, I just meant – ”

“ _Oh_.” Cas says and when Dean glances up, the dude’s pink lips are stretched around a wide, gummy grin. “Actually, I’d like that very much. I assume you want my number?”

“Uh,” Dean can’t believe what he’s hearing. His heart pounds so hard that he can hear it loud and clear. “Uh, yeah. That would be, uh, good.”

Castiel hums happily and then hands him his phone. Numbly – pretty certain that he’s in shock – Dean types his number in and then texts himself. His phone vibrates in his pocket against his thigh.

Cas takes his phone back and with a nod says, “I’ll hear from you soon, Dean.”

“Yeah. Yeah, of course, dude,” he says uncoolly, falling back into his seat as he watches the strangest, hottest guy he’s ever met walk away. His eyes track him until Cas reaches a booth, where a short dude with shaggy brown hair pulls him into a goofy, energetic hug.

“ _Oof_.”

Dean startles and whirls in his seat, only to see Jo leaning against the bar behind him and barely concealing her laughter.

“That was painful to watch, Winchester.”

“Shut up.” He grumbles, hiding his face behind his hands.

“I can’t wait to tell Sam – ”

“Don’t you dare!” He warns, snatching at her phone. She pulls away, cackling like the little imp she is. They play chase like they aren’t fully grown adults in a moderately crowded bar and after an embarrassing amount of time, Dean finally wins, thrusting his hand with the phone in the air and out of Jo’s reach with a triumphant roar. Jo stomps on his foot like the dirty player she is and Dean groans, crumpling enough that she swipes it back with no issues.

In all their fun, Dean hadn’t even noticed the two sets of eyes that followed and observed him. He’d even managed to forget why he and Jo had begun messing around in the first place. He just knows that he hasn’t felt so alive in such a long, long time.


	5. Castiel

**Notes for the Chapter:**

> Hey guys! This is the first chapter from Cas' POV. I hope you guys enjoy! And as always, I'm always happy to hear from you. =) <3
> 
> Also, just to let you guys know, I'm going to start posting one chapter up a week, on Saturdays. =)

Castiel can’t quite look away from the man he’s just met – _Dean_. Dean, with his endearingly shy disposition and impossibly green eyes. The Earth’s most vibrant meadows wish that they could be that green. And beyond their color; how they’d looked at him, like he was the most singularly interesting person in the room. That kind of attention is not something Castiel is used to, especially considering his penchant for strange conversation.

When he’d started delving into the topic of bees and his fondness for them, Dean hadn’t so much as given him a strange look or walked away as most others have in the past. Instead, he’d leaned forward and in the most dazzling way, had asked questions and even laughed at the facts that had amused him. There was something special about him – a hidden story behind the self-conscious twitch of his lips and in the way that he sat taller when he was feeling unsure of himself. Castiel could happily spend hours learning more about him.

But for now, he’s content in watching Dean wrestle with the pretty bartender from earlier. He’s standing on the tips of his toes, black shirt and red flannel riding up _just so_ to reveal the smooth, tan skin of his hip as he dangles a phone over the girl’s head. When Castiel sees the nice, blonde girl stomp on Dean’s foot so hard that he folds over himself with a pained grunt, he gives an empathetic wince. Gabriel must have been watching too, because he does the exact same.

“Well, tickle me impressed, baby bro.” Gabriel says, shifting his focus to the dessert menu in his hands.

Castiel finally drags his eyes away from a sheepish looking Dean to look at his big brother. He rolls his eyes when he sees Gabriel bouncing his eyebrows at him suggestively.

“I’d rather not, if it’s all the same to you.” He mutters, picking up his own menu. The _dinner_ menu. Because he has standards. Standards that would pair nicely with a large, juicy cheeseburger right about now.

“All work, no play. Where did I go wrong with raising you, kiddo? Not enough hugs? Too many ghost stories at bedtime?”

“Michael is the head of the family.”

“ _Michael_ thought he was running a base camp. Are you really about to tell me that he’s the Mike Brady to your _Brady Bunch_ , Cassie?”

Castiel catches Gabriel’s hardened stare and drops his gaze guiltily. “No,” he says gently, thinking of all the times that Gabriel saved him from their oldest brother’s strict set of rules and expectations. _Church is mandatory. Out of bed by 5am every morning. No TV. You don’t have time for parties, you need to study. If I give you an order, you follow it. No questions. Dad’s gone, Castiel, I’m in charge now_ _and I don’t care if you want to be a_ – “No. I’m very lucky to have had you.” He admits honestly. His brother looks guilty too.

“I know he was tough on us. I tried my best to help you, Cas – ”

“You were amazing.” Castiel interrupts, putting his menu down and clearing his throat awkwardly. “Why did you call me here, Gabriel?”

His brother looks thankful for the change in conversation and reverts to his usual, mischievous eyed self. “Oh, we’ll get down to business.” He smirks, dropping his own menu and winking. “ _After_ you tell me everything that happened with Ken Doll over there.”

“His name is Dean.” Castiel frowns. “And nothing happened. We spoke, he bought me a beer and then we exchanged numbers. He was very kind.”

“He bought you a beer? He gave you _his number?_ Cassie, we need to redefine your meaning of ‘nothing happened’. That is not nothing!”

“He invited me to lunch. Of course we exchanged numbers. How else are we supposed to communicate and agree on a time?”

“He invited you to _lunch?_ ”

“Yes.” Castiel says reflectively, the corners of his lips turning up. “I can already tell that Dean is going to be a very good friend.”

“ _Friend?”_ Gabriel gawks. A second later, his head thumps against the table standing between them as he lets out a long, agonized moan. When all Castiel does is quirk an eyebrow at him, he looks up with an equally pained expression. “ _Friend?”_ He groans again, continuing with his dramatics.

Castiel rolls his eyes and, feeling frustrated and confused, asks “that is still the term, yes?”

“Still the – ” Gabriel cuts himself off with a sharp inhale and leans forward in a way that reminds him of all the times that his older brother had drilled lessons of pop culture and party etiquette into his head as a teenager. “Cassie, that twenty out of ten over there doesn’t want to be your friend. He wants to take you out on a _date!_ ”

“A date?” Castiel asks, heart fluttering. He looks in Dean’s direction and manages to catch the man quickly looking away from him as he does so. He smiles. Dean _is_ very handsome and he had listened very intently when he’d talked about the bees. That, and there’s just something about him that screams _good_. He’s not quite sure what it is just yet, but he’s excited to find out. “Do you really think so?”

“Did he say he wanted to be friends?”

“Well, no – ”

“Then yes, Cassie. I think Mr. Bow Legs over there wants to take you out for lunch and then bring _you_ home for desert.”

“Why would he – ?” Castiel’s cheeks warm when he realizes what his big brother is implying. He swallows and suddenly looks very stiff. “I do not think those are Dean’s intentions.” He whispers, voice low and hushed.

“No?” Gabriel smirks. “Why not? You’re a handsome man and almost as importantly, you’re a nice guy too. Why wouldn’t he want to unwrap you like a tootsie pop and figure out how many licks it takes to – ”

“Heyya, fellas.” Castiel sags with relief when the bartender from earlier interrupts their conversation and places two waters on their table. She grins and pulls out a notepad. “My name’s Jo and I’ll be your waitress while our man Ash is on break. Anything I can get you boys?”

“Yes.” He says hastily, collecting their menus and holding them out to her before Gabriel can say anything more condemning. “I’ll have the classic cheeseburger, please.”

Jo takes the menus gratefully and then turns to Gabriel. “And for you?”

“I’m thinking pie,” he says, eyes at full flirty power and his face twisted into a confident smolder. “Any that you recommend, other than the obvious plate of ‘cutie pie’ standing right in front of me?”

“Wow.” The waitress says flatly. “I can’t believe you actually made me listen to that with my own ears. Just for that, I’m charging you extra.”

“Forgive my brother.” Castiel interjects quickly, fixing the man child across from him with a glare. “He thinks he’s funny.”

“Oh, I _know_ that I’m funny.”

“He’s _really not_ and, uh, he’ll take a slice of the apple pie, please. In fact, we both will.” He says politely. When Gabriel raises his eyebrows at him in alarm, he shrugs. “Dean said the apple pie is very good.”

“Oh, did he now?” Gabriel asks, cogs turning. He turns back to their waitress with an impish grin and points a thumb in his little brother’s direction. “You know what? Could you please do us a solid and send a big ol’ slice of apple pie Dean-o’s way? Courtesy of my baby brother here?”

Jo rolls her eyes, but she’s smiling in a way that makes Castiel think that she might just love trouble as much as his brother does. “Sure can. Pie is the way to that man’s heart, after all.” She teases. “I’ll have your orders right up.”

Castiel waits for the girl to walk out of earshot before he turns on his brother, face furious.

“Oh no. That’s the face.”

“ _Gabriel_.”

“I’m doing you a favor, kiddo! You heard the girl. _Pie’s the way to his heart_.” He bats his eyelashes and pretend swoons. “I’m just helping you get laid!”

“I don’t – ” Castiel falters and buries his face in his hands, mortified. “I can’t believe you just did that.” He wallows in his self-pity for a moment and then pauses. Remembering exactly who his brother is, he looks up from his hands and narrows his eyes at him. “Actually, I _can_ believe you just did that.”

Gabriel just sips his water, not at all looking sorry.

He sighs, accepting that this has and always will be his life. “Gabriel. I told you everything about what happened with Dean. Can we ‘get down to business’ now?”

“To defeat the Huns?”

“Is that was this is about?” Castiel asks, tilting his head and sounding particularly troubled. “Gabriel, the Huns are an ancient people and haven’t been active since the sixth century – ”

“Jesus on a tortilla, Castiel! _No_. This is not about the Huns.”

“But you said… ” He looks concerned for a moment and then his eyes widen. “Oh. I did not understand that reference.”

“Clearly.” Gabriel deadpans. His face falls into an unnervingly serious expression and – as if to shield their conversation from spectators – his voice turns softer. “I need your help, Castiel.”

Castiel leans forward, brows furrowed. He doesn’t like the way his older brother looks right now. It reminds him of a time when his brother was still a cop, struggling to help good people against a corrupt system. “Help with what? Gabriel, what’s wrong?”

“It’s messy, Cassie. _Really_ messy and if we do this right, we can end _a lot_ of suffering for a lot of people. It’s a case of a lifetime.”

“A case?” Castiel reels back, uncertain. “Gabriel, you’ve been retired for years. You run the Mystery Spot with Loki. You do _escape rooms_. How did you find a case?”

Gabriel doesn’t falter and instead presses on with more urgency. “I left the force _because_ of this case. I’ve had my suspicions for years and now I finally have the means to do something about it. We can help a lot of people, Castiel, but I need your help. What do you say? Will you be the Starsky to my Hutch?”

“I don’t…” He breathes in and upon seeing his brother’s guarded face, relents. “I’m not sure about this, Gabriel, but I know that you wouldn’t ask me for my help if it wasn’t important. Go ahead. I’m listening.”

Gabriel looks relieved and then dives full-force into an explanation. He only pauses when Jo, the waitress, comes back with their order of pies and a burger. Castiel is pleasantly surprised to discover that Dean is right. The pie is fantastic. It smells of the perfect balance between apple and cinnamon, and tastes like it was made by a doting mother in the 1950s. It’s a pie worthy of its high praise and the burger is just as good. It’s so good, in fact, that Castiel almost tunes his brother out as he enjoys its perfect, smoky flavor.

By the end of Gabriel’s description, Castiel’s chest is tight and he’s aching in a way that he hasn’t in a long time. Even the good food can’t calm him. He understands exactly as to why his brother is so passionate about this case now.

It’s related to Lucifer’s gang.

“He’s our brother, Castiel. I can’t let him hurt anyone else and if this works, we can shut him away for good. For real this time, with no Houdini tricks to help him slip away.”

Castiel swallows and nods. He’s been on the force for three years now and already he understands exactly as to why Gabriel quit when he did. Having Michael as their department’s captain has its advantages, but even Michael – being in such a powerful position as he is – can’t possibly stop every discrepancy in their system. The system has always – and always will be – corrupt. No matter how diligently he and his siblings work to make that not true.

Michael’s more dedicated than anyone else in the entire force in putting their brother away, but Lucifer has always managed to worm his way out of being prosecuted. Every single time. Without fail.

Usually, evidence goes missing or witnesses are bribed – or threatened – into silence. It’s common knowledge that to go against Lucifer means a fate almost certainly worse than death. As a result, not many are willing to testify against him in the first place. But if Gabriel’s sources are as good as they say they are, then maybe his plan might just work.

“Your mole – ” He starts, but Gabriel disarms him with a wave of his hand.

“My mole is good. Believe me. They know what they’re doing.” Gabriel runs a hand through his hair and deflates in his seat, exhausted. “ _The Rack_ is in the center of all of this, Cassie. If we bring that club down, then we bring Lucifer down too. And all the people that have been forced into doing his dirty work and selling themselves can be set free. It’s a win, win, win.” A spark returns to his brother’s whisky colored eyes and somewhere deep within himself, Castiel finds a similar fire forming. He hasn’t felt this way about his work in a very long time – like he can actually make a difference. And yet, there are still so many variables that can go wrong. 

“So,” Gabriel grins, pulling a lollipop out of his pocket and sticking it in his mouth. “Are you in?”

Castiel doesn’t hesitate. “Yes. I’m in.”

“Oh thank God. I don’t think I could have done this without you.”

Castiel rolls his eyes fondly. Gabriel really can’t do it without him – he needs an officer to present the case, the evidence and to place the arrests. Also, to go undercover, considering that most clubs know who Gabriel is.

The ex-cop takes out his wallet, preparing for when they inevitably get their bill. His voice is muffled against the lollipop in his mouth as he speaks. “Oh, and Cassie, one more thing… keep this little thing between us, yeah?”

Castiel’s eyebrows furrow at that. “You want to keep the case a secret?”

“Trust me, kiddo, you don’t want other people knowing. Lucifer has scouts in the force. If they catch wind of what we’re doing, they will put an end to our case and then to _us_. We’ll be dead before we can yell ‘ _Casa Erotica’_.”

“But surely we can tell Michael?”

“ _Especially_ not Michael. I’m sure he’ll enjoy the surprise when we hand it to him completed and neatly tied off with a red bow. Besides, do you really think that he’d let you take a risk like that? He’d be living in constant fear that something would happen to you. It’s best if we leave him out of this altogether.”

“Michael’s been fighting to put Lucifer behind bars since he turned to crime! He’d want to know, Gabriel.” His tone is firm and unwavering, but his brother is even more so. It’s enough to worry him. 

Gabriel leans forward, something imploring and unreadable on his face. “I’m telling you, Castiel. _Do not_ tell Michael. Promise me.”

Castiel looks at his brother for a long time and then nods, mouth pressed into a thin line. “It’s your case. Your call. I promise that I won’t tell Michael.”

“Thank you.” Gabriel says and means it. He leans back into his own space and looks far more relaxed. “Now that I have you on my side, I’m going to start digging up everything I can find on that club. When I’ve assembled a file containing _every little detail_ we may need to know about that place – and I have the go ahead from my mole – I’ll contact you. We can’t dive half-assed into this. If we’re going to be discreet and successfully take Lucifer down, we’ll need to be careful.”

Castiel snorts. Gabriel blinks.

“What?”

“It’s just that I don’t think I’ve ever heard you say that you need to be careful before.” Castiel teases, voice deep and pleasant. “Or that we shouldn’t ‘half-ass’ something. Usually, that’s your thing. ‘Half’ and ‘ass’. You sound so mature.”

“Oh shut up.” Gabriel laughs.

They’re sharing a warm look when two beers are pushed onto their table. Castiel’s half way through saying that they didn’t order them, when he looks up and loses his words in Dean’s eyes.

Dean laughs, eyes crinkled in the corner and an easy grin on his face. Castiel swallows past the heartbeat in his throat.

“I just wanted to say thanks for the pie.” Dean says, his voice an attractive rumble. It’s not dissimilar to the purr of a well-cared for engine. “And uh, goodnight, I guess.”

Castiel can’t help the grin that finds its way onto his face. “Goodnight, Dean. I’m looking forward to our lunch.”

“Yeah,” Dean mumbles, scratching the back of his neck. His cheeks turn a lovely shade of pink and only help to highlight just how many freckles he has. “About that. When is a good time for you?”

“Tomorrow.” Gabriel cuts in, startling them both. Castiel squints and doesn’t trust the wicked look his brother is sending his way. He sounds unnervingly innocent as he continues speaking. “You get a good lunch break at work don’t you, Cassie? What is it, like an hour?”

“So long as it’s not interrupted, yes…”

“Would that work?” Gabriel smirks, turning to Dean.

Dean licks his lips and nods, skeptical. “Yeah, that works.” He turns to Cas and chuckles, obviously hiding his trepidation. “Who’s the wingman, Cas?”

“My brother, Gabriel. The one I was telling you about.” He grumbles, shooting the said trickster a warning look. “Please ignore him.”

Gabriel grabs his chest in mock hurt. “Oh, that’s just harsh.”

Dean shakes his head and looks amused. “Alright. Tomorrow, Cas. Do you want me to pick you up?”

Castiel thinks of Dean pulling up to the police department – where Michael works – and pales. He’d rather not introduce his oldest brother to someone during their first date. That, and his coworkers are all literally nosy detectives for a living. “Actually, I’d like to pick you up if that’s okay?”

Dean looks a little disappointed but nods anyway. “You got it. I’ll text you my work address and a good time tonight. Sound good?”

Castiel’s stomach does a strange flip. “That sounds perfect.”

Dean beams. “I’ll see you tomorrow, Cas. Night.” He turns to Gabriel and waves. “Night, wingman.”

Gabriel waves back and then they both watch Dean go. It’s a pretty sight.

“I wonder if he has a sister. Ooh! Or a brother.” Gabriel swoons. It doesn’t seem to be pretend this time.

“You’re married to Kali.” Castiel mutters, smiling at Jo as she shows up to take Gabriel’s card for their bill.

“She won’t mind.” He says dreamily.

Castiel huffs good naturedly. “You’re impossible.”

“Hey!” Gabriel cries, removing the lollipop from his mouth and pointing it at him. “Careful with your words, baby bro. I just did you a favor of a lifetime.” He winks and pops the lollipop back into his mouth. “Just imagine Dean’s face tomorrow when he sees you pull up _in_ _uniform_ ”

Oh no.

†

When Castiel makes it back home to his apartment, he’s instantly attacked. He chuckles as he bends down to pick up the small ginger kitten clawing at his shoes.

“Grace. We’ve talked about this.”

The little kitten mewls as Castiel holds her out at arm’s length. He melts when those big, blue eyes blink up at him.

“Claws are not how we say hello.”

Grace purrs and Castiel can’t find it within himself to be mad. He brings her to his chest and smiles. Her deep, blissful purr sooths him.

“It’s okay. You’re still learning. Let’s go to bed, hm?”

He takes them both into his bedroom where he carefully places her on his bed and strips down into his boxers. He leaves for a moment to brush his teeth and wash his face and then returns. When he slips under his covers, Grace waddles over to him, her little tail standing straight. She mewls in a demanding manner and Castiel sighs, picking her up and plopping her down carefully onto his chest.

“A please would be nice.”

Grace simply curls into a loose ball and begins to purr again.

Castle hums and allows for his mind to wander as he absentmindedly pets her soft fur. He thinks of Gabriel, of how long he must have been obsessing over this case and why exactly it lead to him leaving the force. He thinks of his mole, the person either incredibly brave or stupid enough to help them put their brother behind bars. And also of Michael, taking in all of his siblings and half-siblings without hesitation after Dad disappeared. He even thinks of Lucifer going rogue out of grief and of all his full-siblings; Balthazar, Anna and Samandriel.

He thinks of the club Gabriel mentioned – _The Rack_ – and thinks of all the people that his big brother said worked there. Of all the men and women who have made deals out of desperation and sell their bodies just to survive. He imagines their suffering and considers how harshly life must have treated them, to chase them so effortlessly into the arms of such an awful place. He stares up at his ceiling, lost in his mind.

And then his phone flashes.

With a grunt and one hand cupped protectively around Grace, he reaches over to pick it up. He blinks against the screen’s brightness and when he sees the message waiting there for him, his heart stutters.

**_Dean Winchester [pie emoji]: Hey, Cas. 12:15, Singer’s Automotive Service and Repair. It’s just outside of town. I’m looking forward to seeing you_ **

Cas’ face lights up and it’s not just the brightness from his phone.

**_Castiel: Hello, Dean. You put a pie emoji next to your name when you typed your number into my phone._ **

The reply comes quickly, but Castiel’s heart still races as he waits. He feels like a teenager; like he’s been thrown back into high school and it’s his first crush all over again.

**_Dean Winchester [pie emoji]: Yeah. To remind you that I’m a cutie pie_ **

Cas huffs indulgingly. It’s a similar joke to the one Gabriel made with the waitress back at the bar and it only makes him feel more comfortable. He ponders Dean’s answer and then starts typing out a reply, when he gets another text.

**_Dean Winchester [pie emoji]: Sorry. I had to._ **

Castiel hits send to his response anyway.

**_Castiel: Did you put an emoji next to my name?_ **

**_Dean Winchester [pie emoji]: Yeah_ **

**_Dean Winchester [pie emoji]: I put you in as Cas and then I put a bumblebee next to your name_ **

**_Dean Winchester [pie emoji]: I know that’s kind of lame, but you sounded like you really liked bees._ **

**_Dean Winchester [pie emoji]: I can change it if you want_ **

**_Cas [bee emoji]: No, that makes me very happy. I love the bees. Goodnight, Dean._ **

**_Dean Winchester [pie emoji]: Night, Cas. Sleep tight, don’t let the bed bees bite._ **

“They would never.” Castiel mumbles to himself, smiling as he tucks his phone away for the night. He falls asleep without difficulty, Grace already out cold on his chest. And when he dreams, he dreams of impossibly green meadows and bees and the sweet, sweet taste of cinnamon flavored apples. And of his brother Gabriel running up to him, eyes wild as he begs for help.

And then the bees and the apples are gone.


End file.
